The Transaction

Excessive admin work and poor-performing sales plays are killing SDR effectiveness and, in turn, company growth. We just so happen to know just the B2B sales expert to help SDR leaders kick things up a notch, wherever they may reside around the globe.Besides having a wonderful British accent, which Craig loved, David Wilkins is the Founder of SDR Leaders of EMEA and the Co-Founder of SDR Leaders of USA and APAC. David joins Co-Hosts Craig Rosenberg and Matt Amundson to dig into how sales leaders are overcoming the major issues facing SDRs (Sales Development Reps) in B2B sales today. David shares how successful sales leaders are implementing AI tools to cut down on excess admin work for their SDRs, why sales channels like cold-calling & video messages are outperforming email outreach, and how dialing up the difficulty of the sales training for your reps can keep them cool as can be on even their most cantankerous sales calls.Plus, David outlines the totally standard, run-of-the-mill journey of how he went from studying at the second-worst university in the UK to working for the number-one mayonnaise manufacturer in the Netherlands and ended up getting into B2B sales. Also, Craig references a late-80s rap duo, Matt alludes to the promise of a brisket, and Producer Sam somehow manages to ask a decent salestech question after breaking the 4th wall earlier in the episode.Critical TakeawaysExcessive admin work is still eating the SDR role alive. In a surprising number of B2B companies, SDRs are still burning three-plus hours a day on manual admin tasks. That is not harmless busywork in B2B sales; it is precious selling time being quietly set on fire. Rather than replacing a human SDR with an AI avatar, target this admin & sales prep work for elimination with AI. Email-first outbound has run out of runway. Email still has a place, but it should be just one piece of a larger outbound strategy that focuses more heavily on better-performing tactics like cold calls and social media touchpoints. The practical implication for sales and marketing leaders is simple: email can support the motion, but it cannot be the whole motion anymore.Sending videos and voice notes through LinkedIn messages works because they do something most outreach still does not: they make it obvious a real, honest-to-goodness human being is on the other end. That is especially useful in B2B SaaS, where copy-paste messages have saturated email, text, and even DM inboxes, and being able to interrupt that pattern buys sellers the few seconds of attention they need to make inroads.The sales training you provide for your SDRs and AEs should be significantly harder than anything they might deal with on a standard sales call. That way, if they find themselves in a delicate situation, they have the skills to stay calm and continue moving the conversation forward. A great way to give your sales reps more, well, reps is to use a training tool with AI-avatars of different customer profiles in sales scenarios.Chapters00:00 - Episode Preview00:51 - Trans-Atlantic Holiday Customs and Re-Ranking of Meats 04:11 - Introducing David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert06:55 - David's Journey From a Terrible School to Amazing Mayo & Eventually a B2B Sales Job15:10 - Why SDR Leaders Don't See Headcount as The Solution for Success with Sales Development in B2B SaaS 30:18 - Why Cold-calling Beats Email for Engaging with Prospects34:59 - Video Messages & Voice Notes Break the Pattern of B2B Sales Outreach46:09 - Improving Sales Training with AI Avatars To Help SDRs Perform Better on Sales Calls49: 57 - Predicting the Future Evolution of the SDR Role in B2B Sales & GTM55:04 - Random Rap & Wrestling References Before Wrapping UpJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Make the training harder than the game.” - David Wilkins“ Making this function what it is, which is a critical part of the revenue generating organization.” - David Wilkins“ I'm gonna be calling myself Ron now, if ever I get in trouble” - Ron DavidsonConnect with DavidLinkedIn: https://www.linkedin.com/in/daveewilkins/ SDR Leaders of EMEA Website: https://sdr-leader.com/ ShoutoutsLars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales?utm_campaign=post-expanded-share&utm_medium=web Travis Henry: https://www.linkedin.com/in/travisjhenry/ Russell Hearl: https://www.linkedin.com/in/russhearl/ PG.aiTitanXNooksHiya Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ QuibblySynthesiaTavusHyperboundScott AlbroRodney-O & Joe Cooley: https://youtu.be/BynWb6swQ74?si=_7ykfGXyz0GDACRl Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Kacie Jenkins is the Head of Marketing for Claude Code at Anthropic. Prior to joining Anthropic, Kacie led marketing at Sendoso as SVP of Marketing, Sourcegraph as VP of Marketing, and Fastly as VP of Marketing, to name a few.Kacie joins co-hosts Craig Rosenberg and Matt Amundson to unpack what B2B brands need to learn from B2C companies in order to build bold, unforgettable brands that increase revenue and redefine markets. Plus, Kacie outlines why B2B startups need to see building a founder brand as a pipeline engine, how to move beyond broken marketing attribution systems, and why brand marketing is making a massive comeback.Also, Kacie shares the outcome of all her speakers getting food poisoning before an event, Craig explains why he’s bringing his son to Vegas, and Matt states his stance on the existence of ghosts. Critical TakeawaysFounder-led brand and content works because buyers want conviction from the people shaping the company, not just polished messaging from the brand account. The key to building a strong founder brand is finding the intersection of three things: 1. What is the founder an expert at? 2. What makes the founder utterly unique? 3. What does the target audience want and need?A bold brand doesn't mean punching competitors; it means being so weird, human, and mission-driven that people can't stop thinking about you. At Fastly, this meant leaning into engineer culture with quirky campaigns (literal messenger pigeons), bright red branding mirroring the founder's personality, and taking public stands on internet ethics. Find what makes your company authentically different and lean all the way into it.Your founder is the person with the most conviction on your team, and that conviction is what cuts through noise in crowded categories. Marketing should treat building and amplifying the founder's narrative as a top priority, not a side project. Invest time sitting with the founder to uncover what they stand for, what they hate, and what future they're building — then help them show up consistently.Sales leaders should map executive posts, thought leadership clips, and campaign creative to relevant strategic accounts, then use that content to multi-thread and re-engage deals. When a founder or visible executive has market credibility, reps get warmer entry points and stronger follow-up moments.Values only count when customers can feel them. If the brand story stops at messaging, buyers will eventually spot the gap. For example, Fastly’s brand worked because their stance showed up in customer selection, customer success, and even how they defined who they wanted to win with in the market.Chapters00:00 - Episode Preview00:51 - Spooky Baseball02:20 - Introducing Kacie Jenkins, Head of Marketing for Claude Code at Anthropic05:46 -  Accidentally Hosting a Spooky Customer Advisory Board Retreat12:53 - What Happens When All Your event Speakers get Food Poisoning19:03 -  How Founders Can Seize the Story of Their Category and Own The Narrative35:48 - How to Build Bold Brands for B2B SaaS41:22 - Why brand fails without founder buy-in47:23 - Marketing Attribution is Broken. Now what?Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The key to winning is real, true, authentic differentiation.” - Kacie JenkinsConnect with KacieLinkedIn: https://www.linkedin.com/in/kaciejenkins/ Anthropic Website: https://www.anthropic.com/ Claude Code Website: https://claude.com/product/claude-code ShoutoutsRuby James: https://www.linkedin.com/in/rubyjameslinkedin/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Artur Bergman: https://www.linkedin.com/in/crucially/  Katie Penner: https://www.linkedin.com/in/kathrynpenner/ Kris Rudeegraap: https://www.linkedin.com/in/rudeegraap/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Udi Ledergor is the Chief Evangelist at Gong and is firmly amongst the upper echelon of the, as yet to be founded, B2B marketing leader hall of fame, having led outstanding teams as both a Vice President of Marketing and Chief Marketing Officer at five B2B SaaS companies for over two decades. Alongside steadfast co-hosts Craig Rosenberg and Matt Amundson, Udi shares how he has crafted one of the top SaaS brands without losing its exceedingly human touch, how Gong thinks about the content they create as part of their marketing strategy, and to use AI to raise your bar for creative thinking by filtering out the obvious crap.Plus, Udi unpacks the three critical marketing leadership lessons he learned the hard way when a mistake in an email marketing campaign almost spiraled into a massive issue for one of the premier B2B SaaS brands in Silicon Valley today.   Also, Craig admits to claims he confused someone on a call, Matt waxes poetic about a B2B SaaS company he doesn’t work for, and Producer Sam revels in an ever-elusive mention of the show notes. Critical TakeawaysWhen a marketing mistake goes public, marketing leaders need to act decisively within hours, not days, and own it personally. A swift action paired with a personal response can de-escalate most complicated situations and help to quell even irate customers. By quickly taking personal accountability for the issue, you can turn a brand crisis into a trust-building moment.Teams should treat complaints as a signal, not the sample size. If a dozen people took the time to complain, many more probably felt the same way and stayed quiet. That is a strong operating principle for brand, product, and customer comms teams: they should respond to the unseen audience, not just the visible inbox.A key to building Gong’s human-feeling brand was deliberately connecting "trusted thought leader" with "relaxed, friendly person who wants to help you out" during an early brand workshop. Most B2B brands default to authoritative-plus-stuffy; product marketers and brand teams should explicitly codify an approachable, human counterweight in their brand guidelines.Use AI suggestions to find and filter out the obvious crap that everyone else would do in their marketing strategy. LLMs are a synthesis of (pretty much) everything on the internet, which means they’re great at telling you about what’s already out there. The next time you’re coming up with ideas for a marketing campaign, ask your LLM of choice for its recommendations and use those as a guide for what not to do.Rather than going fully with either gated or ungated content, using them in tandem can increase visibility and conversions. When sharing ungated content publicly, link to relevant gated assets and resources from within the ungated piece of content. This way, you get the visibility benefits of ungated content while getting your gated assets in front of a larger target audience.Chapters00:00 - Episode Preview00:56 - Craig Flounders While Filibustering to Find an Excuse For His Profile Photo Fiasco03:16 - Introducing Udi Ledergor, Chief Evangelist at Gong05:46 - 3 Critical Marketing Lessons Learned from an Email Campaign that Almost Ruined a Massive B2B SaaS Brand17:02 - How Gong Intentionally Built an Authentic, Sincere, & Human Brand for A B2B SaaS Startup22:06 - Reimagining B2B Marketing Events To Optimize for Guest Experience28:48 - Using AI as a Quality Filter for Marketing Ideas33:36 - The Two Ways to Use AI in Your Work35:19 - Where Gong Lands in the Gated-versus-Ungated Content Debate45:26 - The Basics of Email Marketing That Still Work in B2B47:45 - The Bait & Switch Twitter Play for Boosting Web Traffic For Startups51:31 - How Gong Develops its Content Marketing and Distribution Strategy TogetherJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“We're sometimes over-reliant on all this automation crap. We like that it saves our team work, but we don't realize what we're giving up in return.” - Udi Ledergor“The worst thing that can happen to you is not that some people hate what you're doing. The worst thing that can happen to you is indifference.” -  Udi LedergorConnect with UdiLinkedIn: https://www.linkedin.com/in/udiledergor/ Gong’s Website: https://www.gong.io/ Udi’s Book: https://a.co/d/0Cix9Ll Udi’s Website: https://www.udiledergor.com/ ShoutoutsRuby James: https://www.linkedin.com/in/rubyjameslinkedin/ Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’ Episode: https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisisMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-inBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: https://open.substack.com/pub/thetransaction/p/rebuilding-b2b-customers-confidenceKyle Lacy: https://www.linkedin.com/in/kylelacy/ Top Swear Words - Gong: https://www.gong.io/blog/how-cursing-impacts-sales Alec Paul: https://www.linkedin.com/in/alecjpaul/ Alec’s Episode: https://open.substack.com/pub/thetransaction/p/becoming-a-linkedin-master-with-alec Danny Hutto: https://www.linkedin.com/in/dannyhutto/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

We’ve got the perfect guest to help you understand how your brand can stand out and provide a uniquely incredible experience for customers in the AI era.Stacey Epstein is the CEO of Structured, the only AI-native channel marketing platform purpose-built for complex partner ecosystems. She is also the Host of AI’ve Got Questions, a casual, candid podcast for marketers trying to make sense of the fast-moving world of AI. Stacey joins co-hosts Matt Amundson and Craig Rosenberg to discuss why your positioning framework needs to be at the core of every marketing campaign, how hiring for taste drives differentiation, and how to inject the voice of your customers into your brand.Plus, Stacey shares how to maximize the impact of your CEO or Founder throughout your marketing.Also, Craig talks about the miracle of birth, Matt mixes up the abbreviations of an African country, and Producer Sam expounds on the etymology of the word “czar”. Critical TakeawaysBefore you start executing any marketing tactics, you need to develop a strong positioning framework that clearly articulates what your company does, why it matters, who the buyer is, and what makes you different. Way too many B2B companies are still doing "random acts of marketing" where every campaign differs from the website messaging, creating inconsistent brand experiences that confuse buyers and dilute impact.As AI handles more aspects of content creation, campaign distribution, and administrative tasks, marketing teams should prioritize hiring "tastemakers" who demonstrate exceptional judgment in evaluating strategic creative decisions. The ability to curate, refine, and elevate work, whether human-made or AI-generated, matters more than the ability to execute tactical tasks manually.Treat your S-1 as the foundation for all Go-To-Market activities. It should be the basis of your positioning, informing everything from why you exist, what your product does, points of competitive differentiation, and your future visionOrganizations need a centralized AI leader, whether in marketing ops, revenue ops, or IT, to coordinate AI initiatives across functions and prevent teams from burying themselves in disjointed AI projects. This role ensures strategic alignment, prevents redundant tool purchases, and helps teams focus AI adoption on high-impact use cases rather than experimenting randomly.Chapters00:00 - Episode Preview00:42 - Craig’s Story of Endings and New Beginnings02:46 - Introducing Stacey Epstein, CEO of Structured07:16 - Accidentally Sending an Embarrassing Email to Every Co-worker in an Entire Region15:34 - Why Positioning is Foundational to Your Brand and Storytelling21:29 -  How to Get Better Input on Marketing from Founders & CEOs31:58 - What Stacey's Learned about AI From Hosting her Podcast34:54 - Why You Need to Hire “Taste Makers” in an AI-first world41:50 - A Brief Aside on the Etymology of Czar/Tsar43:35 - Why Companies are Hiring GTM Engineers & The Impact They're Having45:58 - How to Lead AI Implementation in Your CompanyJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Who owns AI in the company?” - Stacey Epstein“ I love coming back to use cases, because use cases come back to the benefit for the company. So instead of telling me what the product does, tell me how that would be used.” - Stacey EpsteinConnect with StaceyLinkedIn: https://www.linkedin.com/in/staceyepstein/ Magnetic GTM Website: https://www.magneticgtm.com/ Podcast: https://aivegotquestions.buzzsprout.com/ Structured Website: https://structured.ai/ ShoutoutsDavid Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketLisa Cole: https://www.linkedin.com/in/lisacole01/ 

The landscape of go-to-market in the B2B SaaS world is shifting rapidly, but thankfully we’ve got just the person to help you get ahead and innovate.James Kaikis is the Founder of GTMshift, Co-Founder of SolutionExec, Co-Founder of AI Sales Studio, and Host of The GTMshift Interview Series. James joins Matt Amundson and Craig Rosenberg to unpack the evolving role of sales reps, how to use the GTM Innovator’s Framework to stay up on AI advances, and why B2B SaaS companies must refocus their GTM motions on their customers.Plus, James shares his top spots to eat in Chicago.Also, Craig calls Matt a technical buyer, Matt rates Craig’s follicular health, and Producer Sam forgets how math works. Critical TakeawaysTechnical buyers have done extensive research before ever talking to you and know their problems better than you do. Stop running rigid qualification frameworks like BANT or MEDDIC that waste their time asking questions they've already answered internally. Instead, get straight to demonstrating how your solution solves their specific problem with their actual data, positioning yourself as a consultant helping them buy rather than a salesperson trying to extract information.Sales reps must be able to demonstrate the product themselves for lower-complexity solutions, especially when selling to other sales or marketing professionals. If you're selling sales technology but can't give a demo because "that's what SEs do," you've already lost credibility with your buyer. Invest time learning your product deeply enough to have hands-on conversations, or accept that AI-proficient competitors will replace you.Shift your focus from new logos to customer expansion. B2B SaaS companies are now generating more net new revenue from existing customers than new logo acquisition for the first time. Every customer you close should have a clear expansion roadmap within the first 90 days, with multiple upsell opportunities identified before implementation completes.Vertical SaaS represents one of the few remaining competitive moats as horizontal solutions get commoditized overnight by AI. Sales reps must develop deep expertise in specific industries—understanding regulatory requirements, workflow nuances, and sector-specific language that generic reps cannot replicate. For example, if you're selling into pharmaceutical, financial services, or manufacturing, you need to speak their language authentically or technical buyers will immediately dismiss you as lacking credibility.The traditional AE role that handled prospecting, discovery, demoing, forecasting, product knowledge, and closing is fundamentally broken because it asks too much of one person. Your role must narrow to being a customer-centric problem solver who builds trust and delivers value, while AI handles pipeline generation and SEs handle technical depth. Sales professionals who cannot adapt to this narrower, more specialized role will be replaced by solutions engineers who understand the product deeply and can build trust through hands-on demonstrations rather than sales techniques.Chapters00:00 - Episode Preview00:50 - Checking in on Craig’s Follicular Growth, Grooming & Glasses03:12 - Introducing James Kaikis, Founder of GTMshift09:06 - The Life-changing Impact AI Innovation Had on James23:17 - B2B SaaS has Forgotten about the Customer & Their Experience31:18 -  The Changing Role of Sales Reps & Why Your Next Account Exec Should be a Solutions Engineer41:02 - How the Next Generation of Sales Reps will be Trained & Interact with AI50:11 - The Opportunity for Experiential Selling that AI Makes Feasible59:04 - Quick Review of the Chicago Cuisine SceneJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“We have lost sight in B2B SaaS of who matters.” - James Kaikis“Trust and value are the ultimate currency and this next wave of B2B SaaS.” - James KaikisConnect with JamesLinkedIn: https://www.linkedin.com/in/jameskaikis/ GTMShift Website: https://gtmshift.com/ AI Sales Studio Website: SolutionExec Website: https://solutionexec.com/ The GTM Shift Interview Series: https://gtmshift.com/the-gtmshift Linktree: https://linktr.ee/jkaikis ShoutoutsDoug Landis: https://www.linkedin.com/in/douglandis/ Doug’s Episode: https://open.substack.com/pub/thetransaction/p/overcoming-outbound-challenges-with Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ David Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Episode: https://thetransaction.substack.com/p/building-an-ai-first-go-to-market MIT Study on AI Adoption: https://mitsloan.mit.edu/ideas-made-to-matter/productivity-paradox-ai-adoption-manufacturing-firms Craig’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/everything-s-back-on-the-table-why-ai-is-revolutionizing-gtm-with-craig-rosenberg Jeff Margolese’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/the-solution-exec-guide-to-navigating-the-great-ai-shift-with-jeff-margolese Dave Brock: https://www.linkedin.com/in/davebrock/ Dave’s Episode: https://open.substack.com/pub/thetransaction/p/really-knowing-your-customer-with?utm_campaign=post-expanded-share&utm_medium=web Trivoli Tavern: https://www.trivolitavern.com/trivoli Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Surprise: Doing ‘more with less’, doesn’t actually work in B2B marketing, and today’s guest has the data to show it.Omar Akhtar is the Founder and Principal Analyst of Benchmarker and the Director of Content at UserTesting. Omar joins co-hosts Matt Amundson & Craig Rosenberg to dive into the B2B marketing data from Benchmarker’s latest survey, why the most successful companies are spending more on brand than demand, and how events have emerged as one of the top growth channels in go-to-market.Plus, Omar digs into when to prioritize paid versus organic channels in your marketing mix.Also, Craig outlines the plans for his kid’s booze-fueled birthday party, Matt laughs at an inopportune moment, and Producer Sam says ‘raccoon’. Critical TakeawaysDoing more with less is dead. You can’t cut your way to growth. Marketing leaders need to choose between efficient growth or exponential growth and spend accordingly. The companies that are actually hitting or exceeding their targets are spending at least the same, if not more, on brand as they are on demand. The companies that are performing the worst are overspending on demand over brand marketing.When new account growth is the priority, marketing teams should lean into paid search and paid social even though they’re expensive, because these paid channels can deliver faster growth and can outperform organic channels for reach.Dinners and small events can be great, but you can easily ruin them by being overly pushy and sales-y. If someone is talking product before anyone’s had a drink, you need to nip that in the bud. Also, some consultants can be pitchy, so invite them selectively.SaaS marketers are great at deploying amazing new tactics; however, on the whole, they lack a strong foundation in the marketing basics. Before you learn about the next bleeding-edge tool, take a minute to brush up on the building blocks, like positioning, targeting, and messaging.Chapters00:00 - Episode Preview01:23 - Introducing Omar Akhtar, The Founder of Benchmarker03:54 - A Perilously Precipitous Sales Call06:01 - How Omar Moved From Rockstar to B2B Marketing Analyst12:26 - Craig’s Dog Crashes the Party in Multiple Ways13:32 - What Benchmarker’s Data has Revealed about Successful B2B Marketing Teams21:26 - Why the Best Marketing Teams are Spending More on Brand Marketing23:56 - Where Content Marketing Fits in the Modern B2B Marketing Mix30:34 - Events & Small Dinners are Converting Like Crazy, but Please Don’t Overdo Them37:24 - No Amount of Great Marketing Can Overcome a Crap Product, Have a Good Product & Execute the Basics of Marketing Well44:11 - What Makes Clay’s Marketing So Special50:21 - How Gong Survived the Latest SalesTech Revolution & is Now ThrivingJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ This idea that we used to have for a long time, where you have to do more with less doesn't hold true anymore, because you can't cut your way to growth anymore.” - Omar Akhtar“We’re really in a B2B SaaS recession.” - Omar AkhtarConnect with OmarLinkedIn: https://www.linkedin.com/in/omarbilalakhtar/ Benchmarker Website: https://www.benchmarkerdata.com/ UserTesting Website: https://www.usertesting.com/ ShoutoutsAmy Holtzman: https://www.linkedin.com/in/aholtzman/ Amy’s Episode: https://open.substack.com/pub/thetransaction/p/crafting-an-exceptional-event-marketing?r=3iae7z&utm_campaign=post&utm_medium=web Udi Ledergor: https://www.linkedin.com/in/udiledergor/ Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode:  https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis?utm_campaign=post-expanded-share&utm_medium=web Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in?utm_campaign=post-expanded-share&utm_medium=web Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

For our first episode of the new year, we’re thrilled to welcome special guest Kathy Macchi,  the Executive Vice President, Innovation & Co-Founder at Inverta.Kathy joins co-hosts Craig Rosenberg & Matt Amundson to discuss where so many go-to-market leaders go wrong with their segmentation, why your message matters more than the channel you deliver it through, and how to design a successful mid-market marketing org amidst massive pressure for budget cuts.Also, Craig bemoans eating vegetables, Matt gives an update on Craig’s health, and some may have been kidnapped at Producer Sam’s house. Critical TakeawaysBefore chasing hyper-specifc and fancy AI tools, codify ICP, targeting, messaging, and what “good” outreach looks like. Then use AI to scale research and execution (with humans judging output), instead of hoping automation will invent strategy from scratch.If the account list is wrong, everything downstream gets harder (sales cycle, conversion, retention, even CSM load). Institutionalize segmentation by use case and continuously prune/refresh the target universe instead of debating tactics in the abstract.Stop obsessing over which channels you’re using and start focusing more on whether you have something worth saying to a specific buyer group. Then should ship that personalized, relevant message across every relevant channel as an integrated system, not as disconnected one-off campaigns.Chapters00:00 Harrowing Health Foods, Rave Recaps, & Tennis Talk08:30 Introducing Kathy Macchi, Co-founder at Inverta12:40 The Business Concerns Coming up In CMO Councils, Primarily AI & Budget Cuts18:43 Why Cultivating Good Taste Transcends AI Advancements & Solving The Problem Before Adding AI Tools30:27 AI's Impact on B2B Marketing Jobs and Economy32:37 Rethinking Marketing and Business Processes with AI34:06 The Role of Effective Targeting for Account-Based Marketing in the AI-era37:02 Effective Use of AI in Marketing42:13 Messaging + B2B Marketing Channel Strategies and Multi-Channel Marketing53:04 B2B Sales and Territory PlanningJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The who is everything” - Kathy Macchi“ We forgot that early pipeline, until you figure it out, costs money.  It costs money and you're going to fail.” - Craig RosenbergConnect with KathyLinkedIn: https://www.linkedin.com/in/kathy-macchi-aa148b/ Inverta Website: https://www.inverta.com/ ShoutoutsGeoffrey Moore: https://www.linkedin.com/in/geoffreyamoore/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Carlos AlcarazDavid Boskovic: https://www.linkedin.com/in/dboskovic/ Our Episode with David: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketOmar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

If you feel like your pipeline is broken, your CAC is bloated, and your dashboards are lying to you… you’re FAR from the only one. Joining the show are the Metrics Brothers, Ray Rike and Dave Kellogg! Ray is the Founder & Chief Evangelism Officer of Benchmarkit, Host of Metrics That Measure Up, a Founding Member of the SaaS Metrics Standards Board, and is an LP at Stage 2 Capital.Dave co-hosts The Metrics Brothers Podcast, writes the incomparable ‘Kellblog’, and is an EIR at Balderton Capital.Dave and Ray join co-hosts Matt Amundson and Craig Rosenberg to discuss the importance of brand investment in the AI age, overcoming the pipeline generation crisis in B2B SaaS, and how GTM leaders can drain the “metrics swamp.”Plus, Dave divulges which SaaS metrics he finds loathsome and Ray shares his unique method for calculating Marketing CAC.Also, Craig airs an ambrosia-related grievance, Matt unveils an old school tactic he’s still using, and Producer Sam falsely announces an exclusive scoop on The Transaction. Critical TakeawaysTreat answer engine optimization (AEO) as a real channel, not a buzzword. As answer engines and generative AI search tools aggregate from dozens of sources but surface only a few. Meaning that you either show up in the top 2-3 responses or you effectively disappear. Teams should build use-case-level content, distribute it widely, and make it novel enough that answer engines want to quote it, while also building their own audience (newsletter, podcast, communities) so they’re not fully dependent on Google’s (or ChatGPT’s) algorithm.Inbound hand-raisers are a much better primary brand KPI than ‘share of voice’ measurements. Watch what percent of qualified pipeline and new ARR comes from inbound hand-raisers. GTM leaders should explicitly target a higher share of pipeline from inbound, track its close rates and ACVs versus outbound, and use that to justify continued brand and content investment.Focus more on the number of opportunities and cost per opportunity, not just total pipe. Revenue teams should watch both volume and dollars by source, so they can see, for example, whether brand-driven inbound is generating fewer but much better-quality opportunities and adjust their mix and SLAs accordingly.If you want overall efficiency, use Marketing CAC (sales + marketing over new ARR); if you want to compare programs, use pipeline generated divided by demand-gen program spend only. GTM leaders should keep CAC reserved for the full go-to-market machine, then use pipe-to-spend for campaign and channel decisions, excluding fixed headcount so they understand the ROI of the next incremental dollar.Sales and marketing leaders must acknowledge the current “pipeline crisis” in B2B SaaS, characterized by insufficient pipeline coverage and declining efficiency. Teams should track both the volume and cost of pipeline generated, and forecast pipeline coverage across all sources (marketing, SDRs, alliances, PLG, etc.) early and often.Aligning on metrics is a long-term, iterative process that requires persistence and cross-functional buy-in. Chapters00:00 Episode Preview01:48 Introducing Ray Rike and Dave Kellogg, The Metrics Brothers05:40 How GTM Leaders can Escape from their ‘Dashboard Hell’11:08 Which Metrics Matter to Your Board18:37 Overcoming The B2B SaaS Pipeline Crisis24:38 The Difference Between Search Engine Optimization & Answer Engine Optimization29:52 Why Brand Still Matters in the age of AI & How to Measure Brand45:21 Why B2B Marketers Need to Measure both Opportunity Count & Cost Per Opportunity47:38 Why Pipeline Coverage Ratio is so Critical for B2B SaaS Startups51:21 Examining Tantalus & The Cultural Impact of Ambrosia in All of Its FormsJoin our Newsletter to get bonus content & never miss an episode: https://thetransaction.substack.com/Epic Quotes“The faster growing companies actually are spending more on brand than on demand.” - Ray Rike“ My least favorite SaaS metric? Rolling four-quarter pipeline.” - Dave Kellogg“ Branding is marketing without a call to action.” - Dave KelloggConnect with Ray & DaveRay’s LinkedIn: https://www.linkedin.com/in/rayrike/ Dave’s LinkedIn: https://www.linkedin.com/in/kelloggdave/ The Metrics Brother Podcast: https://podcasts.apple.com/us/podcast/the-metrics-brothers-fka-saas-talk/id1687214133 Metrics that Measure Up Podcast: https://podcasts.apple.com/us/podcast/metrics-that-measure-up/id1525571613 Benchmarkit Website: https://www.benchmarkit.ai/ Dave’s Blog: https://kellblog.com/ Balderton Capital: https://www.balderton.com/ ShoutoutsRay’s first Episode on The Transaction: https://open.substack.com/pub/thetransaction/p/harnessing-the-magic-of-metrics-with Avinash Kaushik: https://www.linkedin.com/in/akaushik/ Avinash’s Newsletter: https://www.kaushik.net/avinash/marketing-analytics-intersect-newsletter/ Avinash’s SEO vs AEO article: https://www.kaushik.net/avinash/ai-age-marketing-bye-seo-hello-aeo/ Omar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/ Benchmarker: https://www.benchmarkerdata.com/ Exit Five: https://www.exitfive.com/ Our Episode with Dave Gerhardt: https://open.substack.com/pub/thetransaction/p/ai-idea-starters-influencers-and Carilu Dietrich: https://www.linkedin.com/in/cariludietrich/ Our Episode with Carilu: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your Jon Miller: https://www.linkedin.com/in/jonmiller2/ Our Episode with Jon: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in Udi Ledergor: https://www.linkedin.com/in/udiledergor/ Bill Macaitis:

With so much attention within the go-to-market world paid to marketing and sales, account management, which is arguably just as important, rarely gets its due.Alex Raymond is the Founder of AMplify and Host of the Account Management Secrets podcast. Alex joins co-hosts Matt Amundson and Craig Rosenberg for the first major discussion on the podcast of account management and its crucial role in growing revenue and overall company value for SaaS vendors. Plus, Alex breaks down how CROs should organize their team, what types of people make for the best account managers, and why in-depth stakeholder mapping of customer accounts is so critical to growing revenue. Also, Craig mixes up country singers, Matt discovers a great path, and Producer Sam compares someone’s comment to military ordinance. Critical TakeawaysAccount management should be positioned as the "growth department" of your company, responsible for driving profitable revenue from existing customers. Shift the mindset from reactive support to proactive growth, ensuring account managers are empowered and resourced to expand accounts, not just retain them.Start building account management capabilities early, even before you hit $10M in revenue, so you can learn from customers, reduce churn, and set the foundation for compounding growth. Don’t wait until churn or customer growth becomes a problem you’re hearing about in your board meetings.Ambiguity about who owns customer growth leads to missed opportunities. Great account managers are creative problem solvers with strong business sense, often with consulting backgrounds. They should be able to see the big picture, ask insightful questions, and build long-term relationships, rather than just focusing on renewals or incremental expansions. PS: former consultants make for great AMs.Build Robust Stakeholder Maps and Engage at Multiple Levels.Vendors need to actually do QBRs (Quarterly Business Reviews). Go talk to your darn customers.Chapters00:00 - Episode Preview01:00 - Trouble with Tickets03:44 - Introducing Alex Raymond, Founder of AMplify05:59 - The Role of Account Management in The Growth of B2B Startups12:27 - The Power of Exponential Thinking for Entrepreneurs16:01 - A Quick Sidebar about Business Events and Dining in Boulder19:31 - Why Account Management is a Revenue Function & When Your Startup Needs Account Managers29:15 - Where Account Management Should Fit in Your Revenue Team’s Organizational Design 36:26 - What To Look for When Hiring Great Account Managers42:03 - When Account Managers Should Be Brought into New Deals49:13 - Developing Complex Stakeholder Maps for Customer AccountsJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ The CRO should be managing the entirety of their revenue cycle, not just some slice of it.” - Alex Raymond“ Land and expand has never been more important than it is right now.” - Alex Raymond“ I just never, ever want to be a CEO.” - Matt AmundsonConnect with AlexLinkedIn: https://www.linkedin.com/in/afraymond/ Website: https://www.amplifyam.com/ Podcast: https://www.amplifyam.com/podcast ShoutoutsCraig’s Episode on Alex’s Podcast: https://www.amplifyam.com/account-management-secrets/why-post-sale-is-still-broken-and-what-to-do-about-it-craig-rosenberg Mike Rapp: https://www.linkedin.com/in/michaelrapp-intelepeer/ Alex’s Episode with Mike Rapp: https://www.amplifyam.com/account-management-secrets/serve-retain-sell-how-account-management-builds-revenue-leaders-mike-rapp  Dr. Benjamin Hardy: https://www.linkedin.com/in/drbenjaminhardy/  Conscious Entrepreneur Summit: https://consciousentrepreneur.us/ The Science of Scaling by Dr. Benjamin Hardy & Blake Erickson: https://a.co/d/eTUlHeV 10x is Easier Than 2x by Dan Sullivan & Dr. Benjamin Hardy: https://a.co/d/1kf8tSe Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

The immense hype around AI agents is positively palpable, but is there value in adopting an army of AI minions today or is the promise of agentic AI still fictitious pulp?Here to help illuminate and elucidate the role of AI agents is Gabe Larsen, the Chief Revenue Officer at Signals and the former Chief Marketing Officer of Kustomer. Gabe joins co-hosts Matt Amundson and Craig Rosenberg for a deep dive into how agentic AI coupled with signal-based marketing succeeds in go to market where Account-Based Marketing failed in its execution. We get into whether startups should build or buy the tools they need, which new metrics your board might be looking for, and what customers really want to hear about from vendors.Plus, Gabe bids goodbye to the age of software tools while welcoming in the AI-powered teammate economy.Also, Craig vehemently denies accusations of scowling, Matt shares his preferences on the intricacies of the English language, and Producer Sam asks a dumb question.Critical TakeawaysAgentic AI tools need to provide omni-channel execution in order to offer real value and impact to sales and marketing teams. The combination of Signals + Agents outperforms Account-Based Marketing in the way it has been traditionally deployed. However, the core ideas of ABM, such as Ideal Customer Profiles, Target Accounts, Personalization, etc., still hold true. In fact, the advances in AI-powered martech have now made the original promise and vision of ABM possible.In the build vs buy debate, much of what has been built and is being built in-house is far too brittle to accommodate the regular use of a revenue team. You don’t want your whole custom-built workflow to break every time someone makes a minor change to something as small as an email subject line. However, the solutions that are going to succeed and ultimately be bought must be capable of handling the custom needs and workflows of the users. If the available tools are too rigid for customers, then they will look to build their own workarounds, solutions, and eventually, replacement tools.As the “customization economy” takes hold, go-to-market teams should seek vendors that offer flexible, customizable solutions rather than rigid, templatized products. From the vendor side, take note that buyers are gravitating toward platforms that allow them to tailor workflows to their unique needs, and if you fail to provide this flexibility, you will be left behind.Customers crave real guidance from vendors, not just hype about the new features you added. The most successful vendors will be those who offer clear, prescriptive playbooks and best practices (Think HubSpot or Marketo).Chapters00:00 - Episode Preview02:16 - Introducing Gabe Larsen, the Chief Revenue Officer of Signals04:53 - Learning The Costly Difference between Michael and Michelle 09:23 - Catastrophic Sales Kickoff Stories14:26 - The Dim Sum Disaster17:29 - Why Signals-based Marketing + AI Agents are outperforming Traditional Account-Based Marketing26:15 - Builders versus Buyers & Why Tools are Out and Teammates are In31:56 - The Role of AI in Modern B2B Marketing45:01 - The Future of AI-Powered Workforces48:14 - An AI Vendor's Perspective on Pricing for AI Tools & AI AgentsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“The market’s separating into builders and buyers and I think we’re establishing more buyers.” - Gabe Larsen“ Tools are gone, teammates are in.” - Gabe Larsen “This is the customization economy” - Craig RosenbergConnect with GabeLinkedIn: https://www.linkedin.com/in/gabelarsen/ Signals Website: https://getsignals.ai/ ShoutoutsDavid Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Boskovic’s episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

The vast majority of companies that think they are running ABM (Account-Based Marketing) are not actually running ABM. Not only that, they wouldn’t recognize a real ABM strategy if one came up and slapped them in the face with a stack of direct mailers.Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Market and AI strategies. Davis joins co-hosts Matt Amundson and Craig Rosenberg for an exploration of the current state of ABM (Account-Based Marketing), what it takes to drive impact of using AI in GTM Execution, and how to right-size the B2B marketing tactics to each account. Also, Craig uses a ‘Matt-ism’, Matt distinguishes cuddling from canoodling, and Producer Sam fixes a problem with his face. Critical TakeawaysThere are three core account-based marketing models: Enterprise ABM (1:1 and 1:few), Growth ABM (1:many at scale), and Deal Acceleration (targeted support for individual opps).Shift from short, one-off marketing campaigns to holistic, always-on programs that run continuously throughout the year. Build a playbook of ABM tactics (e.g., webinars, executive dinners, personalized landing pages, LinkedIn ads) and deploy them based on account tier and industry segment. This enables ongoing engagement and better adapts to complex B2B buying cycles.Select and tier accounts based on informed revenue potential, not just logo desirability or gut feel. Analyze first, second, and third-party signals, as well as customer LTV and microsegments, to prioritize accounts for deeper personalization and resource allocation. For example, reserve direct mail and executive engagement for tier one, while using scalable digital tactics for lower tiers.Unify your target account lists across sales, marketing, and customer success to drive alignment and efficiency. Instead of each function working from separate lists, create a single Go-To-Market account portfolio informed by revenue potential and engagement signals. AI can dramatically accelerate research, content personalization, and account list building, but only if you have a clear strategy first. Many companies are underutilizing AI or using it without a defined goal, leading to mediocre results.Chapters00:00 - Introducing Davis Potter, Founder of ForgeX08:00 - Quick Coldplay Concert Conundrum Recap10:00 - Davis’ first ABM Webinar horror story16:00 - Redefining Account-Based Marketing: Beyond the traditional pyramid18:00 - A new ABM segmentation model24:00 - The case for a unified Go-To-Market account portfolio27:00 - Growth ABM tactics that actually scale31:00 - Where AI fits into an ABM strategy  (and where it doesn’t)39:00 - How shadow AI is reshaping GTM45:00 - Reporting, the board deck problem, and the MQL hangover49:00 - What your Revenue Team needs to measure in modern ABM53:00 - Replacing the Market Qualified Lead industrial complexJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“One practitioner can't cover 50 accounts and actually leverage one-to-one.” - Davis PotterConnect with DavisLinkedIn: https://www.linkedin.com/in/davispotter62/ ForgeX Website: https://www.forgex.ai/ Revenue Xchange: https://open.spotify.com/show/7v2449do8UGuLAbilezi29?si=1a56c9a9a18d4550 ShoutoutsDemandbaseSangram Vajre: https://www.linkedin.com/in/sangramvajre/Sam McKenna: https://www.linkedin.com/in/samsalesli/ Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan Gottlieb’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Kerry Cunningham: https://www.linkedin.com/in/kerrycunningham/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon Miller’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 

Rachel Dines is a B2B Marketing expert and advisor to multiple SaaS platforms, where she provides her specialty in deep tech companies with sales-led go-to-market motions. Rachel also writes a SubStack newsletter called Tech Dropout. Previously, Rachel was VP of Product and Technical Marketing at Chronosphere and a Forrester industry analyst turned product marketing leader. Rachel joins co-hosts Craig Rosenberg and Matt Amundson for a raucous romp through the world of building analyst relationships as a new SaaS vendor, the problem with startups having too many use cases, and why your B2B startup’s first marketing hire should really be a product marketer.Plus, Rachel reveals what happened when she gave a friend some less-than-amazing career advice.Also, Craig reveals his fondness for a certain slightly disparaging epithet, Matt releases his pent-up rage, and Producer Sam vows to make certain edits to the episode. Critical TakeawaysBuilding relationships with industry analysts at research firms, such as Gartner or Forrester, is only getting more important for B2B startups and scale ups. By the way, ‘building a relationship’ in this context is not code for just paying to play; we mean actually fostering real human connections with individual analysts, even before you think about paying a dime for a subscription for their firm.If you want your SaaS startup to show up in things like industry analyst reports and ‘magic quadrants’, start by finding and reviewing the evaluation criteria for those reports, which are publicly available. Bonus tip: try to get involved early when criteria are being set. For the ‘self scout’ of your product against the analyst’s criteria, bring in a few PMs (Product Managers) and SEs (Sales Engineers) to help you do a brutally honest self‑assessment, find weak spots, and see what shifts can be made. SEs are great resources to bring in because they are hyper aware of the critical issues with their own product and can provide clear-eyed insights.Pick one use case, one ICP (Ideal Customer Profile), and one persona to focus your go-to-market strategy on. Trying to be all things to all customers from day one is a recipe for dilution of your brand and burnout. Choosing one target (even if it feels narrow or imperfect) lets you focus your go-to-market resources, refine messaging, and build momentum for your company.Your first marketing hire should be a Product Marketer, not a demand gen specialist. Startups need someone who can define and refine messaging, narrative, positioning, not just pushing leads to sales. Without a clean story, demand gen spends often under‑deliver.With analysts, frequent light engagements, such as updates about new clients, features, saas founders turning over data, build familiarity and trust. Much of what shows up later in evaluations or quotes starts with these small, consistent touchpoints.Chapters00:00 - Episode Preview00:50 - Endearing Terms for The Wonderful People from Massachusetts03:27 - Introducing Rachel Dines, Author & Go-To-Market Advisor (Plus, Former Forrester Analyst)07:24 - A Quick Convo about Data Centers & The Mission Impossible Film Franchise10:24 - Giving Your First Solo Presentation as an Analyst with a Heads Up16:18 - Why Startups Need To Engage The Industry Analysts Early On20:22 - How Startups Should Approach Their Initial Analyst Relations Strategy29:35 - Matt Admits What Grinds His Gears31:23 - What Early Stage Startups Can do to Become Number One in the Magic Quadrant34:08 - Startups Should Start with One Segment, User, and Use Case46:51 - Why Your First Marketing Hire Should be a Product Marketer52:21 - Some not so great B2B Marketing career adviceJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“Focus, in the Go-To-Market side especially, is always the greatest Achilles heel of so many startups” - Rachel Dines“Pick a lane and win” - Matt Amundson“I can be bought for tiramisu” - Rachel DinesConnect with RachelLinkedIn: https://www.linkedin.com/in/rdines/ Substack: https://racheldines.substack.com/ Website: https://www.racheldines.com/ How I Hacked the Moon: https://a.co/d/eSYYRWG ShoutoutsScott Mersy: https://www.linkedin.com/in/smersy/ Sam McKenna: https://www.linkedin.com/in/samsalesli/ Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Mission: Impossible - Rogue Nation (Christopher McQuarrie, 2015)The Studio (Apple TV+)Last Week in AWS (Newsletter): https://www.lastweekinaws.com/ Corey Quinn: https://www.linkedin.com/in/coquinn/ CursorWindsurfLovableChris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ SnowflakeDenise Persson: https://www.linkedin.com/in/denisepersson/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Even with all the newest, shiniest AI tools out there, successful, sustainable B2B sales growth is still built on nailing the basic sales skills.To provide a refresher on those basic B2B sales skills and more, we’re thrilled to introduce Tom Murtaugh, the Portfolio Operations Director at Nordic Capital, a leading sector-specialist private equity firm. Tom joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of maintaining deal control, why revenue leaders need to understand the key activities that drive outcomes, and how to get your sales managers up to speed as they become more valuable with the implementation of AI.Plus, Tom helps Craig and Matt perform an autopsy on the failure of the sales enablement movement.Also, Craig once again references TOPO and Matt gets envious of a warm male embrace while also imparting the joys of parenthood.Critical TakeawaysWhat are the handful of activities that have a real impact on moving a deal forward for your company? While most organizations cannot empirically state which activities drive revenue, using modern data tools and call analysis, sales leaders can and should run correlation analyses to pinpoint and scale what top performers do.Sales leaders should be directly involved in late-stage enterprise deals, ensuring there is a clear, actionable joint execution plan for each opportunity. Top-down focus and hands-on deal reviews with sales leaders is critical to exceeding targets, even when the forecast looks grim. This level of engagement cannot be delegated or replaced by process alone.AI can accelerate analysis and experimentation, but it cannot define your core GTM motions or fix broken processes. If you haven’t figured out what works, AI will only amplify confusion. Go-To-Market leaders must first establish and validate the key behaviors and activities that move the needle before layering on automation or analytics. Sustainable revenue growth comes from robust GTM infrastructure, such as processes, platforms, and RevOps, that persist beyond any single CRO or sales leader.Sales enablement programs often fail when led by people without quota-carrying experience, devolving into classroom-style training that sellers reject. Shift to “sales excellence” roles, where former sales leaders who coach reps in the field, ride along on calls, and provide practical, trusted guidance. The most powerful enablement tools are those that let reps learn directly from top performers, such as reviewing Gong calls or shadowing high achievers. Tom shared that new reps who proactively sought out and emulated top sellers ramped faster and performed better. Make it easy for your team to access and learn from real sales conversations, not just static content.Chapters00:00 - Episode Preview03:51 - Introducing Tom Murtaugh, Portfolio Operations Director at Nordic Capital10:09 - How Improving Deal Control Turned Around a Terrible Quarter for Collibra21:02 - Understanding the Key Activities that Really Drive Outcomes in B2B Sales28:21 - Why Training First Line Sales Managers Needs to be a Priority for B2B GTM Leaders42:29 - Why the Sales Enablement Movement Ultimately Failed in Improving B2B Sales Orgs51:21 - The Role of RevOps in Building a Sustainable Infrastructure for the Revenue OrganizationSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Any type of conversational analytics tool is the most powerful enablement tool that's out there right now, and people just need to use it.” - Tom Murtaugh“ Your sales manager is be going to become incredibly, even more important than they are today, because they're going to be the ones that even with a little bit of change, are going to have a lot of leverage over a lot of people.” - Tom MurtaughConnect with TomLinkedIn: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Nordic Capital Website: https://www.nordiccapital.com/ ShoutoutsAmanda Murtaugh: https://www.linkedin.com/in/amandabuck143/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Philip CardiNeil Harrington: https://www.linkedin.com/in/neildharrington/  Scott Albro: https://www.linkedin.com/in/scottalbro/  Jeff Goree: https://www.linkedin.com/in/jeffgoree/ Andy Byrne: https://www.linkedin.com/in/byrneandy/ Michael Hargis: https://www.linkedin.com/in/mhargis/ Pablo Dominguez: https://www.linkedin.com/in/pabtexas/ Echo Valley on Apple TV+ Starring Sydney Sweeney & Julianne Moore (Only rated a 6.3/10 on IMDb)Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

B2B sellers and sales leaders find themselves in the midst of an unprecedented Go-To-Market skills crisis at a time when budgets are shrinking and selling is getting harder.Joining the show once again is the inimitable Chris Orlob, CEO at pclub.io, the #1 Skill Transformation Platform for Revenue Teams. Chris joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into where the current sales skills crisis came from, what sales leaders can do to help improve their sales reps’ skill capacity, and why sales reps should start with getting a concrete understanding of a proper discovery process.Plus, Chris discusses why B2B sales leaders should implement a skill transformation loop into how they train their sales teams.Also, Craig addresses an elephant in the room, Matt bemoans the illegality of ‘hacking darts’ in Foster City, and Sam the Producer laughs at Craig.Critical TakeawaysInvesting only in Sales Process is not enough to help sellers hit their targets, because process only covers what to do. Whereas, Skill capacity doesn't stop at what to do. Skill capacity is what to do, why to do it, and how to do it so that you're building judgment. This way, reps can have audible-ready, rich business conversations that create value for both buyers and customers.When training sales reps on new skills, it’s best to make sure they master one skill before they move on to learning another. This builds skill depth, rather than very shallow skill breadth. Without ensuring competency in one skill before moving on, all you achieve is motion without accomplishment.The first, foundational skill that reps should train on is sales discovery. Having a strong grasp on discovery will help sales reps build stronger additional skillsets. It’s harder to build the other sales skills without having a solid understanding of sales discovery.As companies’ go-to-market motions become increasingly complex, if they don’t address the low skill capacity of their sales team, they incur a growing ‘skill deficit’, which if left unchecked will lead to catastrophic results down the line.Chapters00:00 - Episode Preview02:21 - Introducing Chris Orlob, CEO of pclub.io03:33 - An Instructive B2B Sales Story: How to Interact with Procurement Leaders08:06 - Craig & The Case of The Bloody-Eyed Business Meeting12:19 - The State of the B2B Sales Skills Crisis in Go-To-Market Today25:40 - Discovery is the Fundamental Sales Skills Reps Need to Learn33:24 - How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market44:25 - Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' TrainingJoin our Newsletter: https://thetransaction.substack.com/Epic Quotes“We are in an era of a Go-To-Market skills crisis.” - Chris Orlob“Reps and sellers are drowning in technology, but starving for skills and skill capacity.” - Chris Orlob“AI is not the solution to the skill gap.” - Craig Rosenberg“If they can't build a case for me of how they're going to solve my problem, I don't really want to buy it.” - Matt AmundsonConnect with ChrisLinkedIn: https://www.linkedin.com/in/chrisorlob/ pclub.io Website: https://www.pclub.io/Twitter: https://twitter.com/Chris_Orlob ShoutoutsChris’s Last Episode on The Transaction: https://thetransactionpod.com/episodes/to-gate-or-not-to-gate-content-with-chris-orlob-the-transaction-ep-005 Scott Albro: https://www.linkedin.com/in/scottalbro/  Paul Rosenberg: https://www.linkedin.com/in/paul-rosenberg-0970421/ Ryan Tibbetts: https://www.linkedin.com/in/ryantibbetts/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

The old go-to-market playbook is broken, but in this episode we have a B2B SaaS founder who has actually figured out the new GTM playbook to grow in the current market.This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. David joins co-hosts Matt Amundson and Craig Rosenberg to outline how he and the GTM team at Flatfile developed their new AI-first go-to-market strategy, which is handling ten times the capacity of their previous GTM motions.David shares which of the 3 ways AI is being deployed works best, why you need to hire for individual contributors based on a candidate’s tastes, and why every Rev Ops team needs to hire an AI Engineer in order to stay ahead of the curve.Plus, David regales Matt and Craig with potentially the greatest story that’s ever been told on The Transaction, perhaps even better than ‘Maggots on a Plane.’Also, Craig threatens someone with having to wear a raccoon costume, Matt reveals the secret of what makes Craig great, and Sam the Producer experiments with some AI artwork.Critical TakeawaysWhen segmenting your ICP, segment into micro-verticals of 100–500 accounts, so you can then build tailored value propositions, demos, and collateral for each. AI allows this “luxury” level of personalization, which was once reserved for top accounts, to be applied to all targets. This dramatically improves first-call resonance, increases conversion rates, and differentiates your solution in competitive enterprise sales cycles.AI now allows you to turn things like costly enterprise-grade research into a commodity. Using tools like ChatGPT’s Deep Research or Perplexity you can produce insightful 40+ page market and account reports in hours instead of weeks. Validate quality by testing it with actual prospects. This “luxury” level of diligence, previously reserved for only top-tier accounts, can now be applied to every target at low cost.Having a CRM isn’t good enough. You should use AI to index every past customer/prospect interaction and extract key insights (budgets, pain points, workflows). Make this context instantly available to reps so every future conversation builds on a rich historical foundation.Every RevOps team, regardless of size, needs an AI Engineer to rapidly prototype and operationalize AI tools internally. If you want to remain ahead of the curve, you can’t be beholden to the slow development and innovation of tools from other SaaS companies.Operationalize everything in the company like a product. Treat your revenue org like a software system, debug bottlenecks, design orchestrations, and continuously iterate. The faster your GTM processes can be updated, the faster you can capitalize on new AI capabilities as they emerge.There are three main ways AI is deployed, Automation/Replacement, Augmentation, and Amplification. Amplification gives you the largest potential outcomes. To use the Amplification approach, deconstruct every GTM role into component tasks, give repetitive or low-value ones to AI, and keep humans focused on peaks of expertise like judgment, taste, and relationships.Chapters00:00 - Episode Preview01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch 15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement51:34 - Sam Debuts Some Interesting AI Artwork of DavidSign up for our Newsletter: https://thetransaction.substack.com/Epic QuotesIt is incredibly hard to be optimistic enough about what’s possible” - David Boskovic“Dream your wildest dreams and see if you can make them happen. And if not, put them on the shelf, not for a year, but for a few weeks.” - David Boskovic“Part of what makes Craig great is his curiosity. He’s a lifetime learner.” - Matt AmundsonConnect with DavidLinkedIn: https://www.linkedin.com/in/dboskovic/ Website: https://flatfile.com/ ShoutoutsRory O'Driscoll: https://www.linkedin.com/in/roryodriscoll/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Endgame: https://www.endgame.io/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

80% of B2B buyers are already using AI in some part of their research process. Yes, you read that correctly, and we’ve got a special, repeat guest on the show to help you understand that shift in buyer behavior, how to capitalize on it, and much more.We are thrilled to welcome back AI and marketing expert Sydney Sloan, the Chief Market Officer of G2, to the program on this episode. Sydney joins Co-Hosts Matt Amundson and special Co-Host Scott Albro to explore how AI is being used by buyers when making purchasing decisions, the transition from SEO (Search Engine Optimization) to GEO (Generative Engine Optimization), and where business opportunities are emerging along the ‘AI Gradient.’ Plus, we get into some super tactical ways to improve your review strategy to increase trust and show up in AI search results.Also, Matt fawns over Cursor once again, Scott asks about tweeting at Founders, and Sam The Producer mercilessly throws Craig squarely under the proverbial bus.Critical Takeaways80% of buyers now use AI as part of their research process. In order to actually show up in results from an LLM, brands must embrace Generative Engine Optimization (GEO) by creating and optimizing brand content for people and problems, not just keywords.The best way to get more customer reviews is to embed review prompts in-app via tools like Medallia, Pendo, or Qualtrics. This leads to higher volume, verified reviews without incentives. Work with your product team to operationalize in-app review capture.To influence LLM outputs and improve buyer relevance, encourage customers to describe their specific use cases when writing reviews. This increases your company’s discoverability in AI-generated comparisons and rankings.Encourage founders and leaders to engage with reviews and even respond directly, this signals customer obsession and builds brand trust. Ps. you can pipe G2 reviews directly into Slack (Which is what Kyle Porter did at Salesloft).As AI agents become more integrated into your tech stack, you’ll start to feel the emerging need for an “AI architect” role in RevOps. This person would manage prompt engineering, agent workflows, and orchestration across sales, marketing, and customer systems.Chapters00:00 - Episode Preview00:48 - Introducing Sydney Sloan, Chief Market Officer at G204:15 - The Emerging Go-To-Market Playbook & New B2B Buyer Behavior Study11:25 - How to Use G2 to Rank Your Brand in ChatGPT Results for Best SaaS Tools 15:11 - What Makes G2 Reviews Stand Out & Why You Should Always Respond to Customer Reviews 18:46 - How Founder-Led Companies are Using Customer Reviews Creatively21:59 - How Buyers are Using AI Tools In Their Buyer Journey & To Compare Solutions26:47 - How Generative Engine Optimization Helps Your Brand Show Up in AI Search Results31:59 - Why Enterprises are Using AI Tools More Than Startups33:53 - The Meteoric Rise of Cursor & Which Categories or Niches are Ripe for AI Disruption44:24 - The AI Gradient & Why You Need an AI Architect on Your RevOps Team50:21 - Throwing Craig Under The Bus For Causing a Technical Issue & Wrapping UpSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“What we did six months ago is definitely not what we're going to do six months from now.” - Sydney Sloan“If you haven't yet started thinking about how do you show up in the LLMs, you're behind.” - Sydney Sloan“I don't think you can put all of AI generically into the hype cycle. I think you have to look at it by category or use case.” - Scott Albro“People use different language in LLMs than they do in search engines.” - Matt AmundsonConnect with Sydney SloanLinkedIn: https://www.linkedin.com/in/sydsloan/ G2 Website: https://www.g2.com/ G2.ai: https://ai.g2.com/ Putting AI Into Action Roadshow: https://sell.g2.com/ai-in-action-roadshow ShoutoutsKyle Porter: https://www.linkedin.com/in/kyleporter/ Kyle’s Episode of The Transaction: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers Tim Sanders: https://www.linkedin.com/in/sanderssays/ Guillaume CabaneCursor: www.cursor.soQualified: www.qualified.comClay: www.clay.comHubSpot: www.hubspot.com1mind: www.1mind.comSalesloft: www.salesloft.comGong: www.gong.ioIron Mountain: www.ironmountain.comAirbnb: www.airbnb.comWaze: www.waze.comUber: www.uber.comLovable: www.lovable.so Windsurf: www.windsurf.ai Waymo: www.waymo.com Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Imagine you created a sales process so amazing that it was the only one customers actually enjoyed. Impossible? Today’s guest says no.Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale. Brent is back alongside Co-Hosts Matt Amundson and Craig Rosenberg to share how sellers can help B2B buyers become more confident in their own buying decisions, why “frame making” needs to be part of every seller's mindset, and how to tell powerful, emotionally engaging stories.Also, Craig confronts his own fleeting mortality, Matt says he likes “the big pullout”, and Sam the Producer contributes by swearing.Critical TakeawaysModern B2B buyers are overwhelmed and uncertain. Top-performing reps succeed by helping buyers build self-confidence in their decisions, not by pitching harder or throwing more whitepapers at them.The biggest predictor of successful SaaS deals isn’t objection handling, it’s whether the buyer believes they’re making a good decision. Sales teams should focus on guiding internal alignment and validating the decision process.Stop selling like you’re the expert and start selling like a guide. SaaS buyers want to see and hear what similar companies are doing when in their position. Social proof beats thought leadership when it comes to moving deals forward.Customer indecision is the real killer of your pipeline. B2B Buyers who feel overwhelmed delay action, your job is to make progress feel easy and safe.GTM leaders should train reps to speak with emotional clarity, using language that reflects how buyers feel, not just what they need to know.AI can’t replace human trust in B2B sales. Even as automation takes over task work, the real differentiator in SaaS GTM will be emotional connection and the ability to de-risk complex decisions.Vulnerability builds trust. Whether it’s storytelling, deal coaching, or just acknowledging awkward moments, honesty closes more than clever pitches.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Episode Preview02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines12:26 - The Origins of Brent’s Latest B2B Sales Research16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions48:32 - The Key to Telling Compelling, Emotionally Engaging Stories53:25 - How Addressing the Elephant in the Room, like Bloody Eyeballs, can Create Better Human Connections  Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ When things like that make you nervous, uncomfortable, you don't run away from them you have to run right at 'em.” - Brent AdamsonConnect with Brent AdamsonLinkedIn: https://www.linkedin.com/in/brentadamson The Framemaking Sale: https://a.co/d/iQhqSzq Website: https://www.brentadamson.net/ A to B Insights Website: https://atobinsight.com/ ShoutoutsBrent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyerCoffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 

What if cold calling isn’t dead—but everything we know about it is?From dissecting permission-based openers to dunking on dated tactics, sales experts Justin Michael and Charles Needham make a bold case for why the phone isn’t dead as a sales channel—it’s just misused. Justin Michael, aka the John Wick of executive coaching, is a longtime B2B seller and sales trainer, as well as the Founder of the Justin Michael Method and co-author of The Cold Call Algo. Along with being Justin’s Co-Author on Cold Call Algo, Charles Needham is a bona fide B2B Sales Badass in his own right, being the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Joining co-host Matt Amundson for this episode, Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools.Critical TakeawaysEncouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships.The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement. Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes.Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation.Chapters00:00 Intro01:09 Introducing Justin Michael and Charles Needham02:55 Discussing B2B Sales Strategies and Cold Calling as an effective sales channel03:37 Justin's B2B Sales Stories and Experiences08:07 Charles on Modern Sales Challenges for SaaS Startups13:22 The Emerging Role of AI in B2B Sales Today17:10 Cold Calling Sales Techniques and Best Practices30:29 Debating Cold Call Openers32:53 Unified Theory of Cold Calling for B2B sales39:03 Mastering Tonality and Rhythm during B2B Sales Calls56:26 The Future of Cold CallingSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham“Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham“ People buy emotionally, they justify with logic.” - Justin MichaelConnect with Justin MichaelLinkedIn: https://www.linkedin.com/in/michaeljustin/ Website: https://www.salesborgs.ai/ Get the Book: https://coldcallalgo.com/ Connect with Charles NeedhamLinkedIn: https://www.linkedin.com/in/charles-needham/ TitanX Website: https://www.titanx.io/ ShoutoutsKai-Fu Lee: https://www.linkedin.com/in/kaifulee/ AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee: https://a.co/d/ex6F2Yz David Dulany: https://www.linkedin.com/in/davidkdulany/ Wyzer.aiMike Bosworth: https://www.linkedin.com/in/mikebosworth/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

In the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model and simple SaaS pricing tiers contribute to their success in both raising new funding rounds and recurring revenue. Plus, there's a debate over the relevance of a traditional Go-To-Market team for such early-stage startups creating AI products. We also briefly touch upon Matt's favorite movie, John Carpenter's 'Big Trouble in Little China.'Join the newsletter to get new episodes straight to your inbox! Join here: https://thetransaction.substack.com/Enjoy this episode? Share it with a friend!Believe it or not, even in the tech-fueled world we live in, the number one way podcasts grow is word of mouth. So, if you learned something, lost your cool at something, or laughed at something from the show, give us a hand by sharing this with someone else who will get that same value from the show, regardless if it's education, entertainment, or outrage-inducing.

Everyone's talking about how amazing AI can be, but there’s a real dearth of actionable advice on how to actually put generative AI to work for your sales, marketing, customer service, or other go-to-market team. Well, that was until we talked to this week’s incredible guest…Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts.Critical TakeawaysTrain your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills.Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity.Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team.Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account.AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities.Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children.Chapters00:00 - Episode Preview00:36 - The Fast & The Furious: Silicon Valley Drift07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer16:08 - The Power of Building Custom AI Agents for Revenue Growth22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It?42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI AdvancementsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap“The goal are the outcomes, not the activities.” - Jake Dunlap“Outbound never ends. You cannot take a project-based mindset to outbound.”  - Jake DunlapConnect with Jake DunlapLinkedIn: https://www.linkedin.com/in/jakedunlap/ Website: https://skaled.com/ The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller ShoutoutsDirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u NotebookLM: https://notebooklm.google/ The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 Matt Heinz: https://www.linkedin.com/in/mattheinz/ Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false The Club: https://store.winner-intl.com/the-original-club-p2.aspx Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

1. We are testing a new The Transaction product - The Direct Deposit. The idea is to take something that happened that week and one host asks the other host 5 questions. The result is a 5 minute quick hit.2. For this week's Direct Deposit, we cover RevFest. I'll give you the high level: 🐰 Jen Igartua and the Go Nimbly team killed it. Also, I am leading an unauthorized effort to rename it LoveFest 2026 but Matt Amundson keeps killing it. Lesss go! This is the first edition of The Direct Deposit presented by The Transaction.========================================Subscribe to the Newsletter: https://thetransaction.substack.com/ Follow the Show:- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ - Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/- Sam's LinkedIn: https://www.linkedin.com/in/sam-guertin/ - The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ - The Transaction Website: https://thetransactionpod.com/ Ways to Tune In:- Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz - Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 - YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1 - More Options: https://thetransactionpod.com/subscribe

Scott Albro is back in The Transaction hot seat—and he’s not here to play nice. Scott brings a flame-thrower to traditional playbooks, urging GTM leaders to experiment wildly, think like founders, and stop chasing MQLs like it’s still 2014.Craig and Matt get Scott talking about everything from AI-driven storytelling to "vibe marketing," with detours through SDR history lessons, Red Bull stunts, and the existential crisis of printer ownership. If your go-to-market motion still depends on intent data and white papers… this episode might hurt (in a good way).Also, Craig breaks his keyboard, Matt mentions a little company he likes to call Red Bull, and Producer Sam desperately attempts to curry favor with Scott.Critical TakeawaysThe next wave of breakout companies will be driven by founders who embed themselves deeply into the Go-To-Market engine, not just product. Founder-led GTM creates authenticity, speed, and unmatched customer resonance.High-performing Go-To-Market teams in SaaS-land are shifting from one-size-fits-all playbooks to an experimentation mindset. It’s about making bold bets, measuring ruthlessly, and scaling what works, not chasing the hack of the week.Most so-called intent data is internet exhaust, not evidence of real purchase behavior.The best GTM orgs lead with narrative clarity, tying their solution to a broader shift in the world, anchoring it in customer pain, and delivering it with conviction. Skip this, and no one remembers you.Stunt marketing has a place in B2B SaaS. Think viral launches, bold storytelling, and emotional engagement. It’s not about gimmicks, it’s about being memorable in a world flooded with sameness.Chapters00:00 Episode Preview03:30 – The Go-To-Market Founder Concept07:00 – How Modern Go-To-Market Orgs Win13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers17:00 – Crafting a Resonant Story for your B2B brand21:00 – Aligning Product and Go-To-Market Motions (Finally)25:00 – Convincing B2B Startup CEOs to Experiment30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate36:00 – Storytelling Frameworks That Actually Work for Startups42:00 – Lethal Weapon Posters and Swarms of BeesEpic QuotesSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“If you're not reinventing your Go-To-Market org, you need to have a look in the mirror.” - Scott Albro“Founders can just do things that other people can't.” - Scott AlbroConnect with ScottLinkedIn: https://www.linkedin.com/in/scottalbro/ Shoutouts & Resources MentionedSkosh: https://www.merriam-webster.com/dictionary/skosh Skosh Usage over time: ​​https://books.google.com/ngrams/graph?content=skosh%2Csmidge%2Ctad%2Ciota%2Cmodicum%2Cwhit%2Cscruple%2Csmidgeon%2Cwee%2Cfathom&year_start=1800&year_end=2022&corpus=en&smoothing=3BlandMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/  Lena Waters: https://www.linkedin.com/in/lenawaters/Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

That’s right, no guest on this one, but not to worry, it’s just as insight-filled, yet off the rails, as all of our other episodes that you’ve come to know and love. Co-Hosts Matt Amundson and Craig Rosenberg discuss coming to terms with their go-to-market mid-life crises and how they have gotten up to speed on the latest AI advancements to help them get back in the game. Craig and Matt dig into how they’re using AI tools to create things like AI buyer personas, the impact B2B events are having, and what the new go to market playbook is beginning to look like.Also, Matt reveals his devious guilty pleasure and Craig shares how he lost his children in the desert.Critical TakeawaysInstead of prompting AI like a search engine, leaders should teach their teams to treat it like a colleague. Matt’s breakthrough came when he asked ChatGPT how to build personas and what information it needed to do so. By asking “how do I build X?” instead of “give me X,” teams unlock faster, higher-quality outcomes.Adopt a “Shock & Awe” mindset to break through. The market is saturated and fatigued—practical content alone isn’t enough. As Craig put it, GTM teams need to pair insight with surprise to break buyers’ patterns. Leaders should push teams to experiment with bolder formats, storytelling, or AI-powered personalization that “breaks the frame.”Account Research with AI is now table stakes for sales and marketing teams. Using AI for account research (before, during, and after sales calls) is no longer optional. Craig emphasized this is the new baseline expectation. If your team isn’t using tools like ChatGPT or Perplexity to prep on accounts and individuals before outreach, you’re behind.Before adopting any AI vendor solution, ask: “Can my team do this directly in ChatGPT or another general model?” As Craig noted, many startups at SaaStr were pitching account prep workflows that anyone can already do with a simple prompt.Chapters00:00 Episode Preview03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working06:15 Building a New Playbook with AI in the Go-To-Market Hacker era08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback13:15 Talk to Your AI Tools Like People 17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor25:30 Account Research is the New Minimum – How GTM teams are winning with better prep30:00  Matt & Craig just Want to Watch the World Burn37:00 Events Are Back, Baby – People crave new insights and in-person energy40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands45:00 Video Content: Raw vs. Polished – When it’s time to scale production (and when DIY still wins)50:00 Lost in the Desert: A GTM Parable – Craig’s real-life ATV crisis ends with a 10-year-old roasting himSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ It's the age of the Go-To-Market hacker.” - Craig Rosenberg“ Everybody needs to create a custom GPT. And if you want to know how to do it, just ask it. How do I create a custom GPT here?” - Matt AmundsonShoutoutsMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Kristina McMillan: https://www.linkedin.com/in/kristinamcmillan/ David Boskovic: https://www.linkedin.com/in/dboskovic/ Jill Rowley: https://www.linkedin.com/in/jillrowley/ Jill Rowley’s tweet calling Craig’s Blackberry in 2012: https://x.com/jill_rowley/status/187231284970536960 SaaStrMark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Copy.aiKlarity: https://www.klarity.ai/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Mandy Dhaliwal: https://www.linkedin.com/in/1mandydhaliwal/ Jake Dunlap: https://www.linkedin.com/in/jakedunlap/ James Kaikis: https://www.linkedin.com/in/jameskaikis/ Jordan Crawford: https://www.linkedin.com/in/jordancrawford/ Jordan’s Episode: https://open.substack.com/pub/thetransaction/p/inverting-your-go-to-market-strategy?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

B2B marketers keep making the same mistakes when it comes to events, only to end up asking why they didn’t see any ROI. Thankfully, we knew just the right person to help you improve your field marketing game…Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements. Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word.Critical TakeawaysEvents are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage.Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiencesProspects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind.Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet.Chapters00:00 - Episode Teaser00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ13:46 - Lessons to Learn from the Worst Sales Experience Ever25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands44:44 - Thinking Beyond the Booth When Planning out Your Event StrategySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman“If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman“I rub the thing” - Craig RosenbergConnect with AmyLinkedIn: https://www.linkedin.com/in/aholtzman/ Website: https://cheq.ai/ ShoutoutsEvery Little Step I Take by Bobby Brown: https://youtu.be/P0FKzPfsxA4?si=o3k9Iepu3KwnP1Aa Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Jessica Lin: https://www.linkedin.com/in/jessicalin8/ Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-reportSydney Sloan: https://www.linkedin.com/in/sydsloan/ Scott Albro: https://www.linkedin.com/in/scottalbro/ The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

AI use cases & tactics are moving at a million miles per hour which can make it hard to adopt some of these amazing innovations into your go-to-market strategy. Thankfully, we knew just the guy to have on the show to help us put into practice what otherwise could seem like technological mumbo, and or jumbo.That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements.Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world.Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion.Critical TakeawaysIdentify specific, narrow segments by understanding unique heuristics that indicate a need for your product. For instance, identifying complex sales teams with high traffic who would benefit from LeanData's routing solutions is more effective than broad targeting.You need to understand your customers and their pain before bringing in tools like Clay or ZoomInfo. Sales leaders should spend time with SDRs to gain insights on what truly resonates with prospects, ensuring that any data or tools used are enhancing proven strategies rather than replacing deep understanding.The burden placed on SDRs to make sense of complex data without adequate support is a recurring issue. Leaders should simplify data insights and ensure SDRs are equipped with actionable, digestible information, alleviating stress and improving effectiveness. Adopt a 'pain-qualified' segmentation approach. Identify segments that not only fit demographic profiles but also exhibit specific pain points that your product can address, such as complex routing needs in high-traffic sales teams for LeanData. This ensures messages are highly relevant and more likely to result in conversions.Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Introduction: The Intimidating Box01:07 Mr. Pickles and Misadventures in Pocket Dialing04:42 Craig’s Midlife Go-To-Market Crisis05:31 What’s broken with the Old Go-To-Market Playbooks07:30 What is The New World of Sales and AI13:04 Segmenting and Targeting with Data16:43 Permissionless Value Prop in Action23:25 The List is the Message25:47 Methodology and AI Integration26:55 Understanding Customer Segments29:56 Challenges in Sales and Marketing33:18 Effective Campaign Strategies35:16 Adapting to AI and Market Changes38:37 Purpose of Niche Targeting and SuccessSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“The list is the message.” - Jordan Crawford“Never in my life has there been a more intimidating box than the ChatGPT, Claude, Gemini entry box because for the first time in our lifetimes, and maybe human history, we are the limiters.” - Jordan CrawfordNew TermsPain Qualified Segment: Two to five unique heuristics, often that imply tension.Connect with JordanLinkedIn: https://www.linkedin.com/in/jordancrawford/ Website: https://blueprintgtm.com/ YouTube: https://www.youtube.com/@BlueprintGTM Jordan’s Latest Course: https://pvp.blueprintgtm.com/subscribe ShoutoutsScott Albro: https://www.linkedin.com/in/scottalbro/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved! 

Matt Heinz, the President of Heinz Marketing, is a top 50 Sales & Marketing Influencer and a prolific thought leader in the B2B marketing space. Matt digs into why B2B marketers should invest more in brand as the AI Age progresses, whether the Chief Marketing Officer should report to the Chief Revenue Officer, and why B2B marketers are so terrible at naming products and concepts.Also, Craig ponders the meaning of parabolas, Matt ranks the best men’s hair in B2B Marketing, and Producer Sam gets confused by Craig talking about bats.Critical TakeawaysDevelop a structured approach to AI adoption in Go-To-Market strategies. Instead of engaging in 'random acts of AI,' organizations should create an accountability chart detailing which jobs are better suited for machines and which require human intervention. Personal connections and credibility can differentiate a brand in a noisy market. Efforts should be made to maintain and build these relationships alongside leveraging scalable technology.While marketing attribution is important, it should not solely focus on credit for past actions. It should be used to create a more predictable and reliable path towards future outcomes. Go to market teams need to look at attribution as a tool for driving the right behaviors and actions, rather than merely analyzing past performance.Signals, including “intent signals”, need to be understood in context and not treated as immediate leads. Revenue teams should use signals to inform their understanding of where a prospect is in the buying journey, rather than assuming all signals indicate readiness to buy. This nuanced understanding can improve targeting and engagement efforts.Even as AI and automation take on more tasks, creativity and strategic thinking remain irreplaceable. Teams should focus on leveraging AI for efficiency while reserving creative and complex problem-solving tasks for human talent. This balance can drive innovation and maintain a competitive edge.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Episode preview00:30 Craig Goes Batty and Some Auction Antics04:13 Introducing Matt Heinz, President of Heinz Marketing08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies19:16 Should CMOs Report Up to CROs in B2B SaaS?22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools42:11 The Role of Data & The Cloud Data Warehouse in B2B MarketingSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ We shouldn't be guessing anymore, we should be using the agents to tell us how to improve right away” - Matt Heinz“ If I have more noise and less time, who am I going to prioritize? It's the people I enjoy. It's the people I trust. It's the people I like. That's going to be a huge differentiator moving forward.” - Matt Heinz“ I don't want anybody to think that I'm not down with intent signals. I'm down with signals because right now the hardest thing in the world to do is engage.” - Craig Rosenberg“If you are looking for the solution in the tool, you're bound to fail.” - Matt AmundsonConnect with Matt HeinzLinkedIn: https://www.linkedin.com/in/mattheinz/ Website: https://www.heinzmarketing.com/ ShoutoutsBat Tours in Austin: https://www.austintexas.org/things-to-do/outdoors/bat-watching/ Bert Kreischer’s Raffle Story: https://youtu.be/EsCadHpBdkY?si=GDRoQpWQ9B1Z_55l Coffee with Brent & Matt: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ Joe Chernov: https://www.linkedin.com/in/jchernov/ Steve Woods: Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in Lars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Adam Robinson: https://www.linkedin.com/in/adam-robinson-4b156810/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Anthony Kennada: https://www.linkedin.com/in/akennada/ Chris Walker: https://www.linkedin.com/in/chriswalker171/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Mary Meeker: https://www.linkedin.com/in/mary-meeker-5823ba48/ Simbe RoboticsMperativBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Not a long time ago in a Silicon Valley not too far away, the sales infrastructure of almost every startup was an immature, undisciplined mess… Until a certain former printer salesman turned up in town…Lars Nilsson is the Founder and CEO of SalesSource, but you probably know him from his legendary run as the VP of Global Sales Development at Snowflake. To Craig, Lars is, “one of the masters of the universe in sales development and inside sales and business, and clearly very fit.” Lars joins co-hosts Craig Rosenberg and Matt Amundson to discuss how we got to the current state of sales training and enablement in B2B SaaS, why the GTM Engineer role is the next hire you need to make to improve your revenue team, and whether having B2B sales reps roleplay with AI avatars is the way forward or just a waste of time.Also, Craig relives stories of his past mastication, Producer Sam fights yet another losing battle, and Matt warns everyone that, “ we're going to go deep. We're going deep.”Critical TakeawaysRecognize and elevate the Sales Development Representative (SDR) function within the organization. CEOs and senior leaders should regularly acknowledge the impact SDRs have on pipeline generation. Simple acts of recognition can significantly boost team morale and performance.Create a systematic process to gather and disseminate insights and customer feedback from the front lines of sales. SDRs interact with numerous prospects daily, and their feedback can inform product development, marketing strategies, and sales tactics. Ensuring this information reaches executive levels can align the organization’s initiatives more closely with market needs.Giving your sales team more ‘at-bats’ to practice and hone their craft results in better sellers. Leverage AI-based tools like role-playing bots to enhance SDR training. These tools can provide a scalable, less intimidating way for SDRs to practice their pitches and objection handling. Encourage cross-departmental learning within your org. Facilitate opportunities for SDRs to learn from other teams, such as marketing, operations, and customer success. This cross-training can develop well-rounded employees and ensure smoother transitions when SDRs move into new roles within the company.Consistently produce and share content that showcases successful customer stories and product use cases. Having a dedicated resource person, like the retired beat reporter who worked with Lean Data, can ensure continuous content production that drives engagement and educates prospects.Encourage a culture where continuous learning and improvement are part of daily operations. Regularly update training programs and technology stacks, and stay abreast of the latest trends and tools in sales and marketing to maintain competitiveness.Sponsored Segment~Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Episode Preview00:35 - Craig Eats like Cookie Monster03:13 - Introducing Lars Nilsson, the Founder & CEO of SalesSource and Former VP of Global Sales Development at Snowflake07:46 - The Genesis of Sales Development in SaaS & How it Expanded on Account-Based Marketing Concepts13:23 - How Xerox Trained Their B2B Sales Team and What Startups Should Learn from Their Success21:34 - The Emerging GTM Engineer Role & The Impact Its Having on B2B Sales Teams Using AI Tools34:59 - Should B2B Startups Try to Replicate the SDR Academy from Snowflake38:17 - How Startup Leaders Can Elevate the SDR Role & Why They Must Show Their Appreciation for this Critical Function45:42 - The Importance of AI Roleplaying Tools for Training B2B Salespeople54:11 - Startups Founders Should Play a More Active Role in Developing Their Go To Market StrategySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ I just think that Snowflake with 300 SDRs today, maybe in two years, they'll have 50. But each one will be able to punch above, like they are five individuals because of all the automation.” - Lars Nilsson“ One Go-To-Market engineer today is going to make five SDRs punch like they're 25.” - Lars NilssonConnect with LarsLinkedIn: https://www.linkedin.com/in/lanilsson/ SalesSource Website: https://salessource.com/ ShoutoutsStuart Silverman: https://www.linkedin.com/in/stuart-silverman-32132/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Karan Singh: https://www.linkedin.com/in/karan-singh-29269015/ Travis Henry: https://www.linkedin.com/in/travisjhenry/ Brendan Short: https://www.linkedin.com/in/brendan-short/ Pete Kazanjy: https://www.linkedin.com/in/kazanjy/ Jason Vargas: https://www.linkedin.com/in/jasonvargas/ John Barrows: https://www.linkedin.com/in/johnbarrows/ Becc Holland: https://www.linkedin.com/in/beccholland-flipthescript/ Hyperbound: https://www.hyperbound.ai/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ Kevin Dorsey: https://www.linkedin.com/in/kddorsey3/ Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ Scott Barker trying to book a meeting with Avarra’s AI Avatar Role Play: https://youtu.be/90EQSxcIhqc?si=gKDiVmsnadrsk_IY Tavus: https://www.tavus.io/ 

Most B2B brands (yes, probably yours) think that they’re ‘customer-centric’, and yet none of them ever stop droning on and on about their product and its ‘revolutionary’ features.Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups.Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director.Critical TakeawaysImplement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team.Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours.Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs.Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals.Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Episode Preview00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue06:36 - The Origin Story of Women in Revenue (The group, not the concept)18:17 - The Immutable Impact Diverse Teams in Business23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market AlignmentSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein“ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer)Connect with LaurenLinkedIn: https://www.linkedin.com/in/laurengoldstein/ Winning by Design Website: https://winningbydesign.com/ Women in Revenue Website: https://womeninrevenue.org/ ShoutoutsSydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ Shari Johnston: https://www.linkedin.com/in/sharijohnston/ Jen Dimas: https://www.linkedin.com/in/jenpd/ Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ Jim Walker: https://www.linkedin.com/in/jwwalker/ Robert Koehler: https://www.linkedin.com/in/rkoehler/ RadiusMarketoMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ InsideViewBabcock JenkinsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb MiroMark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Colin Gerber: https://www.linkedin.com/in/colinsgerber/ SocureAdam B. Needles: https://www.linkedin.com/in/abneedles/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with AnnuitasLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.Critical TakeawaysThe crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Episode Preview00:20 - Squishy Pineapples & The 1995 UCLA Bruins04:01 - Introducing Ana Leyva, GTM Leader at Pear VC08:29 Selling at B2B Conferences on the Road as a New Mom 11:32 - Focus on Providing Value, not on Bland “Personalization”21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“I am sick of personalized emails.” - Ana Leyva“I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana LeyvaConnect with AnaLinkedIn: https://www.linkedin.com/in/analeyva/ Pear VC Website: https://pear.vc/ ShoutoutsAJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode: Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCSStevie Case: https://www.linkedin.com/in/steviecase/ Scott Albro: https://www.linkedin.com/in/scottalbro/ GongScott Barker: https://www.linkedin.com/in/ssbarker/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Sheila Stafford is the Founder and CEO of TeamSense and joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into how to land enterprise clients as a startup, how to build out a B2B sales team from scratch, and why NRR (Net Revenue Retention) is the most important metric for founders to focus on. Shelia also shares why she thinks email is a dead sales channel and why she is betting on modern PR tactics for growing TeamSense.Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on.Critical Takeaways NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.”Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings.Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs.Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification.Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Preview & Craig’s Christmas related-shirt04:21 - The Sometimes Life-saving Impact Founding a Company Can Have10:03 - Email is a Mostly Dead Channel14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups33:11 - How Do You Measure the Value Your Product Delivers to Customers & Why Founders Need to Focus on NRR 35:45 - How to Drive Alignment Between Founders and Their Boards38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila StaffordConnect with SheilaLinkedIn: https://www.linkedin.com/in/sheila-stafford-451976b/ Website: https://www.teamsense.com/ ShoutoutsFortiveVantaChristina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Brett Queener: https://www.linkedin.com/in/brettqueener/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Is your main go-to-market channel driving sustainable growth? Good, double down on it, don’t start splitting up your resources into a bunch of other directions.Eric Spett is the Founder and CEO of Scalebound, providing operator-led coaching that helps CEOs scale with clarity and lead with confidence. Many in the audience may know Eric better as the Co-Founder of Terminus and his work evangelizing Account-Based Marketing. Eric joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of focus for founders, why you shouldn’t wait to start selling until you find the perfect pricing model, and the power of in-person events and communities. Also, Craig starts hearing voices and Matt shares his encounter with Andre 3000 in an Atlanta Shake Shack.Critical TakeawaysStay focused on your primary demand channel. So many companies shift focus to secondary channels prematurely. If a primary channel like organic social selling on LinkedIn or cold calling is working well, it’s crucial to thoroughly exploit this channel before diverting resources to a new one.Avoiding "shiny object syndrome" ensures that the company’s energy and resources are directed toward proven strategies and tools that truly add value. It helps in maintaining strategic clarity and ensures the team remains aligned on critical business goals, thereby driving more sustainable growth.Don’t overcomplicate your early-stage marketing strategies. Focus on a single selling proposition. For instance, ZoomInfo successfully built its business purely on outbound tactics. Finding and honing in on the company’s single greatest strength or 'superpower' can lead to substantial growth.Building a community around your product or service can significantly enhance customer engagement and retention. In-person events are a great way to improve the activity and engagement within online communities. Structured, curated communities can lead to higher customer retention and more effective peer-to-peer marketing. This helps in creating a robust, organic promotional network that can significantly impact long-term growth and customer satisfaction.Experiment with new channels and strategies but avoid overcommitting to unproven methods at the cost of what’s already working.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro01:46 Introducing Eric Spett04:21 First Deal Stories and Lessons Learned13:05 Is Your Go-to-Market motion working? Good, Keep doing it.23:47 Navigating Business Growth and Go-To-Market Strategies24:11 The AI Dilemma in Business25:41 Why LinkedIn can be A Double-Edged Sword for B2B Founders34:00 The Power of Community Building for SaaS companies46:14 Concluding Thoughts on Focus and CommunitySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Founders, CEOs, go-to-market executives are so quick to put a lot of focus and eggs in experimental baskets when the thing that they're doing really well is still working really well. Do it and keep doing it, keep your focus.” - Eric Spett“I'm just really bullish on the need for human community and human connection.” - Eric SpettConnect withLinkedIn: https://www.linkedin.com/in/ericspett/ Website: https://scalebound.com/ ShoutoutsSangram Vajre: https://www.linkedin.com/in/sangramvajre/ TerminusAtlanta Tech VillagePhil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Scott’s Episode: https://thetransaction.substack.com/p/helping-every-founder-tell-their?r=3iae7z TOPOEverstringDavid Politis: https://www.linkedin.com/in/davidpolitis/ David’s Episode: https://thetransaction.substack.com/p/narrow-down-your-damn-icp-with-david?r=3iae7z Pavilion: Rob Forman: https://www.linkedin.com/in/robforman/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

It’s painfully pitiful what passes as personalized prospecting presently. However, we’ve got just the guest to help sales reps get back on the right track.Sam McKenna is the Founder of SamSales Consulting and is the foremost expert on social selling and leveraging LinkedIn to drive revenue. Sam and her team are redefining the go-to-market status quo for modern organizations through unmatched sales training and LinkedIn branding. Sam joins co-hosts Craig Rosenberg and Matt Amundson for a very fun and fascinating dive into how to improve your personalized sales messages to prospects, the secrets to successful social selling, and the best time to prospect. Plus, we share stories from some of our worst webinar fails. Also, Craig denies claims that he was in fact the heavy breather while hosting a webinar with Guy Kawasaki a decade ago and Matt reveals the truth about the size of a certain actor’s mouth.Critical TakeawaysSales reps, please take 3 seconds to THINK before sending another stinky, smelly, no-good, automated email to a prospect. If you want to stand out to them and get their attention, earn it by doing the work that none of the other reps reaching out to them won’t. Show them you know them.A simple way to stand out to decision makers at target accounts is to engage with their LinkedIn posts. However, hitting “like” does not qualify as engaging in a way that will stand out. The smart play is to comment something insightful.Prospecting during non-working hours, like weekends and evenings, can capture the attention of busy executives. Emails sent during these times can stand out because prospects are usually less overwhelmed and more likely to engage with content beyond their regular work distractions.Don’t buy a ‘great new tool’ until you know what you’re going to do with it. Figure out how to solve the problem you’re addressing before you ever get close to buying a tech solution.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro Sales Insights with Sam McKenna04:38 Introducing Sam McKenna, Founder of SamSales Consulting08:02 Announcing The New Sam McKenna Award For The Best Guest10:13 A Particularly Titillating LinkedIn Controversy11:44 The Airing of Our Webinar Woes22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator30:24 How to Use Social Selling in SaaS34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator41:44 Why Putting in the Work is the Way to Wow Prospects and Customers45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales RepsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Why is it that so few people will just put in the actual work that that converts?” - Sam McKenna“ Anything that you can't automate won't be done.” - Matt AmundsonConnect with SamLinkedIn: https://www.linkedin.com/in/samsalesli/ Website: https://www.samsalesconsulting.com/ Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/ ShoutoutsHayley Hoad: https://www.linkedin.com/in/hayley-hoad-2565549/ Bobby Axelrod (Billions)Jill Rowley: https://www.linkedin.com/in/jillrowley/ Paige Tills: https://www.linkedin.com/in/paige-tills/ Joy Wilder Lybeer: https://www.linkedin.com/in/joywilderlybeer/ Gail Moody-Byrd: https://www.linkedin.com/in/gailmoodybyrd/ Adam Robinson: https://www.linkedin.com/in/retentionadam/ Adam’s episode of The Transaction: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Toby Carrington: https://www.linkedin.com/in/tobycarrington/ DocuSignON24 MarketoEngagioGuy Kawasaki: https://www.linkedin.com/in/guykawasaki/ Jon Gray: https://www.linkedin.com/in/jon-d-gray/ DailyMail Article about the “LinkedIn Boobs Post”: https://www.dailymail.co.uk/news/article-14406563/linkedin-post-fury-comparing-woman-breast-size-confidence.html Bobby Axelrod/Damian Lewis Tiny Mouth Investigation: https://www.maxim.com/entertainment/damian-lewis-tiny-mouth-2016-3/ Reddit discussion of Bobby Axelrod/Damian Lewis’s tiny mouth: https://www.reddit.com/r/Billions/comments/8jcnx5/anyone_else_getting_annoyed_by_damian_lewis_tiny/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

You’ll be hard pressed to find a more energetic and experienced sales expert than our special guest, Maria Boulden!Maria Boulden has spent over 3 decades creating and leading world-class sales teams at leading enterprise organizations like DuPont and Gartner. She brings her incredible experience in multiple verticals and truly unstoppable energy to one of the best conversations yet with co-hosts Matt Amundson and Craig Rosenberg. Maria drops some serious insight bombs in this one, including why steak dinners aren’t the deal closer that they once were, why top execs need to get down to the frontlines to talk with employees, and why ‘not broken’ is not good enough for your company to succeed. Additionally, there is some great advice in here about effectively leading change management efforts in your organization, why building personal relationships in SaaS has become so important for B2B sellers, and why you shouldn’t hold a deal signing at a Japanese gentleman’s club. Fueled by an ungodly amount of Coke Zero, Maria really brought it this episode and delivered some incredible stories, which make this a must-watch!Also, Craig tests out a new hat and Matt admits he can be bought with a burrito. Critical TakeawaysSenior leaders need to be visibly and vocally present with front-line sellers periodically. This not only boosts team morale but also ensures the leader understands the day-to-day challenges and can directly impart strategic guidance.Sales teams should focus on providing value and building genuine connections rather than relying on traditional wining and dining strategies.Waiting for 'normalcy' to return so you go back to old tactics is not viable. Leaders must guide their teams to adapt to the current market conditions and be prepared for continuous change.Conducting “pre-mortem” sessions can be an effective way to anticipate potential failures and mitigate risks before executing significant strategic changes. This approach can foster an environment of proactive problem-solving and better preparedness among the team.Helping clients understand their own business better and providing insights creates stronger, more trusting client relationships.Sponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro00:44 Craig’s Special Hat02:35 Introducing Maria Boulden10:39 The Challenge with Channel Partners19:31 Brazenly Baring It All23:03 A Quick Conversation Regarding Caffeine23:43 Steak Dinners have Gone Stale in Sales33:42 Stories from the Signing Party & Where NOT to Hold One36:48 Taking a Hands-on Approach to Leadership in Sales38:17 Unbatten the Hatches & Adapting to Market Changes41:56 How Executives Should Engage with Their Sales Teams50:59 Delving into some Delicious Additions to Business Dictionaries55:30 Wrapping UpSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ It was not my aspiration that they would have world-class sales skills, it was my expectation.” - Maria Boulden“ Not broken is not good enough in this environment.” - Maria BouldenNew TermsDonut Run (v): When a rep brings a box of joe and a box of donuts to meet with their distributor and ‘shoot the breeze’ for an hour.Ask Hole (n): Someone who continuously asks the same question, but never does anything with the suggestions they receive.Pre-Mortem (n): A proactive meeting held before executing a decision, campaign, etc., where the risks are clearly laid out along with what indicators should be monitored to determine real-time progress and what actions need to be taken mid-course.Connect with MariaLinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ Website: https://www.jsjrehoboth.com/ ShoutoutsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Post: https://www.linkedin.com/posts/danielpgottlieb_good-luck-with-that-ai-theres-no-ai-on-activity-7293698734540955648-rNIz Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z Nick Toman: https://www.linkedin.com/in/nicktoman/ Nick’s Episode: https://thetransaction.substack.com/p/the-commercial-efficiency-crisis?r=3iae7z Neil RackhamSpin Selling: https://a.co/d/1FSFtS1 Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Kyle Porter: https://www.linkedin.com/in/kyleporter/ Kyle’s Episode: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers?r=3iae7z Brent Adamson: https://www.linkedin.com/in/brentadamson Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Bill McDermott: https://www.linkedin.com/in/billrmcdermott/ GartnerDuPontSalesforceLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Michael King is one of the leading marketing executive recruiters working today and is also the author of a new book, Be There When I Return, a memoir of epilepsy, love, and success. Michael joins co-hosts Craig Rosenberg and Matt Amundson to discuss his personal journey with both epilepsy and his career, along with crucial career advice for marketing leaders looking for their next roles. Michael shares how the CEO should factor into your job search, why you shouldn’t chase titles, and the state of the job market for B2B marketing executives.Also, Craig tries out a new look and Matt relives an epic beach party in Vegas.Critical TakeawaysEnsure the people you hire have relevant experience at companies similar in size and stage to your own. Avoid hiring someone just because they’ve been part of a larger company’s success unless their role aligns directly with what your company needs now.Chase companies over titles. Titles shouldn't be the defining factor when considering new positions. Joining a strong, growing company should be the priority as it offers career growth opportunities in the long run. Focus on the company's potential rather than the initial title, as the ultimate career growth lies in sustainable company success.Sponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro02:58 Introducing Michael King04:15 Michael's New Book & Incredible Personal Journey09:29 Recruiting Career & Success Stories18:54 Amazing Event Marketing Anecdotes27:44 Falling in Love with a Brand28:33 The Importance of Relevant Experience33:55 Chasing Titles vs. Chasing Companies39:14 The Value of Good Companies49:03 Epilepsy Awareness and Personal StoriesSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ If you go to a good company, you will never look for a job again.” - Michael King“ For success in your career, you chase companies, you do not chase titles; you do not chase money, you chase companies” - Michael KingConnect with MichaelLinkedIn: https://www.linkedin.com/in/michaelking/ Website: https://kingrecruiting.net/ Book Website: https://www.michaeltking.com/ Book signing in San Francisco: https://www.bookpassage.com/event/michael-king-be-there-when-i-return-ferry-building-store ShoutoutsGeorge WallaceMaria PergolinoWill Smith & DJ Jazzy Jeff Reunion at Everstring’s Pool Party: https://youtu.be/v6-QoeusjEs?si=2CynMyahkkqG1mT8 Jessica CrossStephanie Stacey EpsteinDavid Mylam Dave ArnoldMichael LundgrenMiles KellyRob BernsteinUdi LedergorRussell UdySuccessFactorsSalesforceBroadvisionOktaCoupaSiebelGongCrestaLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Employee churn is a serious problem that is seldom discussed, especially given how much of a detrimental impact it has on even the best companies. To help illuminate this problem and how to fix it at your organization, Katherine Andruha joins co-hosts Craig Rosenberg and Matt Amundson for a much-needed conversation filled with tips, tricks, and a few flamingos.Katherine Andruha is the Vice President of Business Development at Fivetran and has led top-performing sales teams for decades at cutting-edge SaaS companies such as Simpplr, Cloudflare, Coursera, Eightfold.ai, Anaplan, Apttus, and Aruba Networks.Katherine sheds light on where current onboarding programs fall short and shares what can be done so that employees are actually put in the best position to succeed. Additionally, Katherine dives into the importance of properly managing pipeline progression.Also, Craig recounts getting “flocked”, Matt compliments Craig’s athletic abilities, and Sam the Producer grossly mispronounces someone’s name. Critical TakeawaysA comprehensive onboarding process for BDRs is critical. Make sure new BDRs aren’t making live calls until week four. This allows them to become fully comfortable with the systems, processes, and their pitches, minimizing the risk of errors and increasing their initial successes.Utilize AI tools for mock calls to simulate real-world environments. This allows BDRs to practice handling objections and refine their pitches in a risk-free environment before they contact actual leads. Incorporate various channels such as live calls, LinkedIn voice notes, and personalized videos. Ensure that new BDRs are trained to use these channels effectively as people are now more responsive to phone calls and LinkedIn interactions.Ensure that managers have a consistent checklist for onboarding and supporting BDRs. This will help maintain consistency and high standards across teams.Regularly review pipeline stages to ensure there are no stale leads. Utilize automated reminders for deals that have been stagnant for too long to push progression actively.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro06:30 Introducing Katherine Andruha11:23 Onboarding and Training Challenges19:25 Effective Onboarding Practices for B2B SaaS Companies29:05 The Importance of Confidence in BDRs30:37 The Sales Manager's Role in Onboarding33:26 Territory Ownership and AE Handover35:15 Creating a Fun and Productive Environment as a B2B Seller37:45 Pipeline Progression and Accountability42:48 The Role of CMOs in Pipeline Progression44:57 Closed Lost Analysis and Product Feedback48:01 The Importance of Phone Calls48:41 Using Swag to Engage ProspectsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Know your business. It's the only way you will be taken seriously.” - Katherine Andruha“Just call the leads” - Katherine AndruhaConnect with Katherine AndruhaLinkedIn: https://www.linkedin.com/in/katherineandruha/ Website: https://www.fivetran.com/ ShoutoutsDoug Landis: https://www.linkedin.com/in/douglandis/ Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ Alan Berkson: https://www.linkedin.com/in/alanberkson/ Nooks: https://www.nooks.ai/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

There are more people than ever involved in deals on both the vendor side and customer side, and it’s having a massively negative impact on B2B growth.Nick Toman is the Chief Product and Transformation Officer at SBI (Sales Benchmark Index) and is the third and final co-author of The Challenger Sale we’ve had on the show. Nick brings some amazing new sales and business research to dive into with co-hosts Matt Amundson and Craig Rosenberg. Nick unveils the effect that having more sellers involved has on win rates, the three behaviors of B2B salespeople that lead to the best commercial relationships, and why actions that seem like they would slow down deals are actually the key to closing them faster. Matt sparks an interesting discussion around sales compensation and the impact it has on both the behaviors of B2B sellers and the growth of the company on the whole. Toward the end, Nick teases his new concept of 'Headway Selling,' which focuses on actually helping customers reach their goals rather than simply selling them as much useless crap as possible.Also, Craig recounts his childhood trauma of growing up a Dodgers fan in San Fransisco, Matt practices to be a court stenographer, and Sam the Producer confesses to an affinity for gnomes (?).Join our Newsletter: https://thetransaction.substack.com/Critical TakeawaysNot only have buying groups grown immensely, but the number of people working on deals with those buying groups has also exploded. There are now an average of 12 people in buying groups and 5 people involved with the sale from the vendor side. This has led to a spike in confusion for buyers and a sharp decline in win rates for salespeople.The role of CSMs (Customer Success Managers) has devolved to have an extremely broad remit that is too big for them to actually deliver on effectively. In an ideal world, the CSM role should be to use very clear signals to identify customers who are struggling with adoption or retention issues and help them solve those issues. As it stands, many CSMs provide ongoing services and end up competing with account managers to land expansion and renewal opportunities. The competition on its own is one thing, but once the business is compensating both the CSM and the AM, there’s an issue with cost and efficiency.B2B sales reps need to focus on deeply understanding and aligning with customer initiatives. Sellers should be thinking about how they can help customers grow in their own businesses and avoid roadblocks. Gaining this deeper understanding of customer needs drastically shortens sales cycles and increases deal sizes.There are 4 main archetypes of behavior for people in commercial roles: 1. Narrowing- Closing early, Closing often. 2. Provoking - Provocative insights to redirect customer thinking (AKA: Challenger). 3. Translating - Detail & data-oriented to help customers understand impact. 4. Anticipating - Help customers think through the process and future challenges. Of those 4 archetypes, the two that perform best in sales are Translating and Anticipating. The research showed that sellers exhibiting those behaviors actually closed deals more quickly and for more money than sellers using the Narrowing or Provoking behaviors. Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Coming Up in this Episode...00:40 Will the Real Nick Toman Please Stand Up01:53 Introducing Nick Toman, Co-Author of The Challenger Sale03:09 The Impact of The Challenger Sale in B2B Sales13:55 Commercial Efficiency is Crippling B2B SaaS Growth21:22 Is Sales Commision Getting out of hand for B2B Companies?28:22 Why Don't Buyers Want to Talk to Sellers Anymore?31:05 Key Behaviors for Successful Commercial Relationships33:53 Why Starting Fast Is So Critical for Sales Success All Year Long36:27 Strategies for Effective Sales Execution to Start the Fiscal Year Strong41:08 Understanding The Four Commercial Role Archetypes & Their Impact on Deal Velocity48:54 Customer-Centric Selling and Trust Building53:56 Headway Selling & Delivering Real Customer SuccessEpic Quotes“ You’ve got to help the customer make headway and you don't want to make headwinds.” - Nick Toman“ Commercial efficiency- the yield on dollars spent in sales and marketing- has gone down 50 plus percent.” - Nick Toman“ Those who really do situate themselves in a path of helping the customer evolve their business and get things right do much better than those who are like ‘Buy this thing.’” - Nick TomanConnect with Nick TomanLinkedIn: https://www.linkedin.com/in/nicktoman/ SBI Website: https://sbigrowth.com/ Latest Research - How a Fast Start to the Year Defines Your Growth Outcomes: https://sbigrowth.com/tools-and-solutions/how_a_fast_start_defines_your_growth_outcomes ShoutoutsMatt Dixon: https://thetransaction.substack.com/p/decoding-sales-indecision-with-matt?r=3iae7z Brent Adamson: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z The End of Solution Sales - HBR Article: https://hbr.org/2012/07/the-end-of-solution-sales Dave Brock: https://thetransaction.substack.com/p/really-knowing-your-customer-with?r=3iae7z Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ Neil RackhamHarvard Business Review: https://hbr.org/ Karen Freeman: https://www.linkedin.com/in/karenefreeman/ Stop Trying to Delight Your Customers - HBR Article: https://hbr.org/2010/07/stop-trying-to-delight-your-customers AJ Gandhi: https://thetransaction.substack.com/p/navigating-market-success-with-aj?r=3iae7z Vantage: https://www.vantage.sh/ Ben Schaechter: https://www.linkedin.com/in/bensign/ Marlin Equity Partners: https://www.marlinequity.com/ Gartne...

There’s a lot of confusion about how to find the champion of your product within a buying group.To help sort things out for B2B sellers, we invited Krysten Conner on the show! Krysten is an extraordinary sales coach who is hired by top SaaS revenue organizations to train their sales teams into incredible teams. Krysten has also made a number of courses available for purchase through her website and through pclub.io. Krysten joins co-hosts Matt Amundson and Craig Rosenberg to break down three ways to identify and develop strong champions within the buying group to help you close more deals. Krysten also shares the secrets to mastering multi-threading for sellers and how to maintain deal momentum with prospects so they become customers.Also, Craig shares the playbook he used to land his first girlfriend, Matt adds an “s” where he shouldn’t have, and Sam the Producer puts his foot squarely into his big mouth.Critical TakeawaysThere are three ways to proactively discover a champion within a prospect's buying group: 1. Do they do work asynchronous of your meeting with them? 2. Do they bring other people to follow-up meetings? 3. Do they have a point of view on the next steps?The first person to reach out or take a meeting with a seller is not necessarily the champion within that organization for your product or service. Don’t make the mistake of assuming they are the champion. Talking with you makes them a contact, not a champion, by default.“Typically” is a magic word to use in your sales calls. Buyers are very risk-averse and want to be sure they’re not doing something wrong that will get them fired. By sharing what other buyers “typically” do when it comes to things like next steps, you can give buyers peace of mind. Buyers aren’t experts at buying your product, so you need to teach them and guide them to make the right decision. This process of educating buyers and helping them avoid common pitfalls makes them feel much more comfortable.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Intro03:44 - The "Let Me Help You Get this Car" Story07:24 - Krysten’s Embarrassing Sales Stories13:22 - Develop a Champion, Don’t Wait For Them to Show Themselves18:39 - Examples of Asynchronous Work that Champions will Do25:58 - Champions will Bring More People to Follow Up Sales Calls32:36 - Craig Details how he Landed his First Girlfriend33:35 - Who Should be Doing Asynchronous Work Within The Buying Committee41:54 - Does Your Buyer have a Point of View on the Next Steps44:54 - Mass Email Does Not Count as Multi-Threading51:10 - Who a Champion Is and What They Will Do in The Buying CycleSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ You multi-thread, by single threading.” - Krysten Conner“ When I'm sending actually any email, if it's no one's baby, it's an orphan.” - Krysten ConnerConnect with Krysten ConnerLinkedIn: https://www.linkedin.com/in/krystenconner/ Website: https://krystenconner.com/ Access the Free Slides Krysten Shared in this Episode: https://docs.google.com/presentation/d/1DOf9bsPh0m7WtQxwhlJfT7Yg22LkD3iukivIk0W1cOA/edit?usp=sharing ShoutoutsChris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris Orlob's Episode of The Transaction:Krysten’s Multi-Threading Course with pclub: https://go.pclub.io/multi-threading-masterclass Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/Mark Kosoglow's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseScott Barker: https://www.linkedin.com/in/ssbarker/Scott Barker's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/selling-like-a-real-human-being-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Without a real point of view, your company, your product, and all of your amazing features will drift into irrelevance amidst the soothing currents of the sea of sameness we see in the state of SaaS. (Just learned about this thing called alliteration!)To help you avoid that terrible fate and aid you in developing your positioning, we are thrilled that Bob Wright, the Founder of Firebrick Consulting, joined co-hosts Craig Rosenberg and Matt Amundson on the show. As a B2B Marketing expert, Bob has helped hundreds of B2B companies define and refine their positioning over the last several decades and is one of the foremost authorities on the subject working today.In this episode, Bob illuminates the criticality of ‘selling the problem, not the solution’, why B2B positioning should be a CEO-led initiative, and the three questions that your positioning must answer for buyers.Also, Craig eats the world’s loudest piece of chocolate and Matt tries to hire another guest while live on the podcast.Critical TakeawaysSell the Problem, Not the Product. Focus on identifying and articulating the key problem your product solves for the customer. This creates urgency and relevance in the buyer's mind, making them more likely to engage with your solution.Your positioning should answer three key questions: 1. Why now? 2. How are you different? 3. Why does it matter to the customer? These answers create a compelling narrative that drives customer interest and action.Stop focusing on the features. Emphasize the broader business impact and outcomes in your B2B marketing, rather than detailed product features. This approach resonates better with executive buyers who are more concerned with strategic advantages.Shift from explaining how your product works, to inspiring the customer on why it matters to them. This makes your marketing message more compelling and memorable, driving stronger customer engagement and commitment.Sponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Highlights01:56 Introducing Bob Wright, the Founder of Firebrick Consulting07:36 Differentiate your B2B Brand or Die17:22 Portfolio Positioning Challenges22:00 Targeting the Right Buyers with your B2B Marketing23:55 Expanding into New Markets28:56 Maintaining Focus While Growing31:06 The Importance of CEO Involvement33:34 Effective Business Positioning Strategies37:15 AI’s Impact on Positioning41:52 Measuring Positioning Success for Your B2B company42:48 Analyst Influence and Market Trends44:51 Explaining Positioning to the Board47:11 The Role of Storytelling in Positioning and B2B MarketingJoin our Newsletter: https://thetransaction.substack.com/Epic Quotes“Sell the problem, not the product.” - Bob Wright“Don't waste all your go to market investments on shitty messaging.” - Bob WrightConnect with BobLinkedIn: https://www.linkedin.com/in/findurtruegenius/ Website: https://firebrickconsulting.com/ ShoutoutsAJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ OktaMicrosoftOracleSAPHPEGartnerLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Selling B2B has always been hard. The crazy buying frenzy of the ZIRP era was the exception, not the rule, so if you’re expecting the current buying climate to change any time soon, you need to readjust your perspective.Scott Barker, Partner & Co-founder of GTMfund and Host of The GTM Podcast, joins Host Craig Rosenberg and special guest-host Scott Albro to talk all things sales, venture capital, and go-to-market. Scott (Barker) shares why focus can give sales reps superpowers, the outsized impact of warm introductions when building pipeline, and how focusing on uniquely human skills can help you excel in sales. There’s also some great discussion around the importance of accountability and ownership throughout your go-to-market team.Also, Craig pitches both Scotts on launching a legal practice, Scott Albro relives the glory days of selling TOPO services, and Sam the Producer attempts to crack the case and catch the Bottle Cap Culprit.Critical TakeawaysInvest time in becoming an expert in the problems you are solving for your customers. Offer valuable insights that make clients see you as invaluable.Focus on the human side of sales, including trust-building and relationship management; that’s what closes deals. Rely less on pure automation or technology and more on human connections.Sellers can emulate what works in founder-led sales by using personal testimonies about why they joined the company or how the product solved a problem for them. This can make their pitch more relatable and compelling.Warm introductions are the best way to build pipeline in what is quickly becoming an AI-dominated selling landscapeSponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Intro00:26 Retreading Brent Adamson’s Maggots on a Plane Story02:30 Introducing Scott Barker05:10 Funny Fundraising Stories08:33 The Importance of Humanizing Sales12:59 Overcomplicating Pipeline Generation16:25 The Human Side of Sales19:39 How to Build Trust in Sales22:08 Expertise in Sales: Lessons from TOPO29:46 The Concept of “Opinionated Software”34:39 Overcomplicating Pipeline Generation38:19 The Power of Warm Introductions43:36 Scaling Founder-Led Sales52:59 The Value of Human Skills in the Age of AISign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ If you even have the thought of an excuse as a sales leader, as a seller, as a marketer, you're already dead in my books. It requires full and complete accountability.” - Scott Barker“ If there are things that are stopping you from doing your job, it is nobody else's problem, but your own” - Scott BarkerConnect with Scott BarkerLinkedIn: https://www.linkedin.com/in/ssbarker/ GTMfund Website: https://www.gtmfund.com/ GTMfund’s new fundraising announcement: https://techcrunch.com/2025/02/04/how-max-altschuler-accidentally-founded-a-vc-firm-that-just-raised-another-54m/ GTMnow Website: https://gtmnow.com/ The GTM Podcast: https://gtmnow.com/tag/podcast/ ShoutoutsBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent Adamson’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Max Altschuler: https://www.linkedin.com/in/maxaltschuler/  Javier Soltero: https://www.linkedin.com/in/jsoltero/ ZendeskAnthropicMicrosoftGoogleNeil Harrington: https://www.linkedin.com/in/neildharrington/ Jim Cyb: https://www.linkedin.com/in/jimcyb/ Vinny Pazienza, AKA Vinny Paz and Vinny “The Pazmanian Devil" PazienzaBleed For This (2016, Ben Younger)Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

When your buyer isn’t confident in the decision they’re making, they will choose not to decide. Meaning, that you’re not going to close that deal, which is a serious problem in B2B.To help solve that problem, we’re thrilled to welcome Brent Adamson, the co-author of The Challenger Sale and renowned sales speaker, to the show. Brent joins hosts Matt Amundson and Craig Rosenberg to discuss the crucial sales topics in his new upcoming book, The Framemaking Sale. They get into the problem with value-selling, why sellers need to teach buyers how to buy with confidence, and where thought leadership is falling short in today’s environment.Also, Craig pitches an idea for a radical new podcast and Matt cuts to the front of the line to call dibs.Critical TakeawaysFocus more on building customer confidence in their own decision-making abilities rather than just showcasing the value of your product. If customers are reluctant or unsure, they will likely delay or avoid purchasing altogether.Bring implementation and customer success representatives into pre-sale discussions. This helps reassure the customer that post-sale support will be robust and demonstrates your commitment to their success.Instead of just showcasing customer success stories, position them as a tool to show customers how to buy so that new customers understand the buying process and pitfalls to avoid. This gives prospects practical advice and increases their confidence in making a complex decision.Optimize your sales process to lose deals quickly. If a deal is likely to be lost, aim to lose early rather than late. This saves your sales team time, resources, and focus for more promising opportunities.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Trailer01:25 - Introducing Brent Adamson03:51 - I’m Tired of these MFing Maggots on this MFing Plane10:08 - The Impact of Buyers’ Low Confidence in Themselves18:42 - Buyers Don’t Know How to Buy23:44 - Implementing a Objectives, Tactics, Results Approach to Sales30:49 - The Problem with Replicating Successful Sellers36:26 - Thought Leadership & Content Marketing’s Role in Building Confidence40:49 - How to Building Customer Confidence45:16 - The Role of Founders in Sales51:39 - Wrap UpSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Solve for customer’s confidence in themselves” - Brent Adamson“ It's not that I'm selling badly, it's that customers are buying badly.” - Brent AdamsonConnect withLinkedIn: https://www.linkedin.com/in/brentadamson Website: https://www.brentadamson.net/ A to B Insights Website: https://atobinsight.com/Maggots on a Plane Video: https://youtu.be/BFp30CkVcLo?si=aDSKIeQOTfyt9IZ5 ShoutoutsKarl Schmidt: https://www.linkedin.com/in/karl-schmidt-q/ Bryan Smith: https://www.linkedin.com/in/bryankeithsmith/ Tyler Harnish: https://www.linkedin.com/in/tylerharnish/ Marc Benioff: https://www.linkedin.com/in/marcbenioff/ Sense-making for Sales in HBR: https://hbr.org/2022/01/sensemaking-for-sales  Matt Dixon: https://www.linkedin.com/in/matthewxdixon/ Stephen Powell: https://www.linkedin.com/in/stephen-powell-06996785/ Kevin Hendrick: https://www.linkedin.com/in/kevinhendrick/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

When you can tell your story in a compelling, confident way, you can change the lens through which everyone views you, your accomplishments, and your potential.Dia Bondi, a TEDx speaker, author of Ask Like An Auctioneer, and executive coach, joins Hosts Craig Rosenberg and Matt Amundson for an exceedingly energetic and entertaining conversation focused on communicating effectively as a leader. In between some fun tangents, they dig into how to uncover and craft your origin story to tell a more compelling narrative, why doing live demos on stage needs to go the way of the dodo, and how to raise more funding without a pitch deck. They also discuss their favorite examples of leaders who are actually doing this well and showing the world who they really are. Strap in for a fun and informative fifty-two minutes that every aspiring leader needs to hear (or watch if you’re on Spotify or YouTube).Also, Matt mixes up 1960s movie characters named Felix and Craig channels his inner Sully as he desperately attempts to land multiple planes.Join our Newsletter: https://thetransaction.substack.com/Critical TakeawaysWhen someone asks you who you are, don’t rifle through the bullets of your resume. Instead, tell them the narrative of your origin story. Include the core things that drive you, the context around why you set out to do X, and who you really are.Speaking on stage is too expensive for you to have a live demo of your product that doesn’t work. It’s much better to have a pre-recorded demo for your presentation and then give people an opportunity to interact with a live demo at your booth where things are lower stakes if the product fails.Founders need to realize when to hand off the tactical duties in their all-hands meetings, such as being the emcee or running a slide deck. Your team needs you to show up at the status that matches the role that people need you to play in the world.All-hands meetings are extremely expensive, especially the ones that are run poorly and time-intensive. You need to allocate your team’s time carefully based on what is most important to the company’s mission, so make sure not to squander that precious time.Being a compelling communicator is not about being perfectly polished, it’s about staying true to yourself and adapting your natural approach to each context while maintaining authenticity.Sponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Intro00:20 - Craig comes Straight Outta Compton00:58 - Fun Facts about Dia Bondi, Matt, & Softball04:09 - Introducing Dia Bondi08:20 - The Impact of Establishing Your Voice12:13 - What is Founder Unrest & When Does It Show Up?15:19 - How Founders can Find Their Own Voice & Unlock Their Origin Story20:42 - Why Understanding How to Tell Your Origin Story Matters31:12 - Dump the Live Demos from your Presentations33:15 - Wait, How Expensive are All-Hands Meetings?38:20 - Two Big Misconceptions about Communication43:44 -  Examples of Leaders with Great Perspectives & Well-Developed Voices50:04 - Craig Compliments Sam for Displaying Basic Competence50:24 - Wrapping UpEpic Quotes“ Founders are always going into conversations that are bigger than their britches. That's kind of like a job requirement.” - Dia Bondi“ To win and to differentiate today, we need the founder to reach trusted superstar status as fast as possible.” - Craig Rosenberg“ I think of founder voice as something you lend to your venture.” - Dia BondiConnect with DiaLinkedIn: https://www.linkedin.com/in/dia-bondi/ Website: https://www.diabondi.com/ Dia’s TED Talk: https://youtu.be/mFtHKTgyjyU?si=oElL9kWENAiSMary Ask Like An Auctioneer (Book): https://www.asklikeanauctioneer.com/ Dia’s Resource Library: https://www.diabondi.com/resources New Terms: Buttwing (v): To guesstimate. See Also: BallparkShoutoutsClaire Sua-Amundson: https://uclabruins.com/news/2013/4/17/208207255 Claire Pitching to Dan Le Batard: https://youtu.be/o-HM5Sm5omA?si=3yzu1TtT_tD5mUyq Funny Article about Claire and Matt: https://vault.si.com/vault/2005/06/06/-hitting-the-big-time Dan Le Batard: https://lebatardaf.com/ The Odd Couple (1970-1975)Howard Schultz: https://www.linkedin.com/in/howardschultz/ Howard Schultz Interview on Acquired: https://youtu.be/A0fvX-wV70Y?si=-Ljn1jqTYP5aGEaR Starbucks: https://www.starbucks.com/   Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Jensen Huang Interview on Acquired: https://youtu.be/y6NfxiemvHg?si=bfv8w-1wgTZk5l6A Nvidia: https://www.nvidia.com/en-us/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ David Solomon: https://www.linkedin.com/in/david-m-solomon/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Justin Gray, author of the brand new The Go-to-Market Cheat Code and Co-Founder of In Revenue Capital joins Hosts Matt Amundson and Craig Rosenberg to share how to build more effective and efficient B2B partnership programs, why nothing seems to be working in marketing, and his cheat codes to go-to-market success in B2B. Justin explains how and why LeadMD evolved from being a competitor to building an extremely strong partnership with Marketo. There’s also a great discussion about what VCs and other investors look for in founders when investing in startups and how this has changed in recent history.Also, Matt vehemently opposes accusations of being hyperbolic and Craig recants on one of his ill-concieved New Years resolutions.Critical TakeawaysThe success of any partner progam depends first and foremost on executive alignment. Without buy-in from leadership, 99% of B2B partnerships will fail.No matter how good your content may be, you still have to earn the right and access to get your content in front of your target audience by building strong relationships.Stop looking for copy and paste playbooks to use that are being used by everyone else in the market. If you don’t you’ll just be adding your content and brand to the endless pile of lifeless, gray ooze of things that get ignored. Take a risk and you’ll at least have a chance of sticking out.Any partner motion begins with building a relationship with one person. Find the right people to focus on and start one at a time. This is a much quicker way to build real relationships and trust than trying to boil the ocean and make a play for everyone at once.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Introducing Justin Gray00:50 The Origin Story of LeadMD and how they Partnered with Marketo09:55 The Go-To-Market Cheat Code Book16:47 Craig makes fun of Justin’s Office18:12 Lessons on Relationships from The Wild West of the Payment Processing Industry30:26 The Cycle of Innovation and Imitation32:09 The Importance of Knowing Your Buyer40:34 What Venture Capital looks for in Founders46:50 Building Effective Partnerships1:05:02 18th Book Plug of the EpisodeSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ What's working is what has always worked which is trusted relationships” - Justin Gray“Innovators look for ideas” - Craig RosenbergConnect with JustinLinkedIn: https://www.linkedin.com/in/inrevenue/ The Go-to-Market Cheat Code (Book): https://inrevenue.capital/cheat-code/ Order The Go-to-Market Cheat Code on Amazon: https://amzn.to/4hjtrbA In Revenue Capital Website: https://inrevenue.capital/ The GTM Cheat Code (Podcast): https://inrevenue.capital/insights/?article_category=podcast ShoutoutsEssentials/Fear of God Clothing: https://fearofgod.com/ FocusMAAS ImpactChris Selland: https://www.linkedin.com/in/cselland/ LeadMDMarketoBill Binch: https://www.linkedin.com/in/bill-binch-302a4a2/ Margaret Hoogerbeets: https://www.linkedin.com/in/mhoogerbeets/ Amy Guarino: https://www.linkedin.com/in/amyguarino/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Scottsdale Princess: https://www.scottsdaleprincess.com/ Josh Wagner: https://www.linkedin.com/in/joshwagneraz/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon Miller’s Post about the Tragedy of the Commons in Marketing: https://www.linkedin.com/posts/jonmiller2_mpb2b-b2bmarketing-marketingautomation-activity-7262460572032483328-hs0J? Dirty Money, Season 1, Episode 2: https://www.netflix.com/us/title/80118100?s=i&trkid=258593161&vlang=en Bessemer: https://www.bvp.com Nick Mehta: https://www.linkedin.com/in/nickmehta/ Marc Beniof: https://www.linkedin.com/in/marcbenioff/ Founder’s Fund: https://foundersfund.com/ Asher Mathew: https://www.linkedin.com/in/ashermathew/AWS Marketplace: https://aws.amazon.com/marketplace Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Every Founder has a story to tell and by telling that story in a compelling way, they can give their company an outsized advantage and the leg up they need in order to grow.The founder of multiple companies and a veritable thought leader in his own right, Scott Albro, joins Hosts Craig Rosenberg and Matt Amundson, for a rollicking romp through the big AI questions now getting asked, the fundamentals for building a successful founder brand, and how to create high-quality content that is worthy of your buyers’ time and attention.The crew dives into an intriguing debate over whether AI Co-Pilots or multitudinous AI Agents will win out in the future as AI is integrated into more go-to-market jobs and processes. Scott shares his three-part framework for helping founders tell compelling stories and everyone, including Sam, shares their favorite examples of successful founder brands.Also, Craig is complimented on his militaristic sleeping abilities and Matt begins the long journey to recovery by admitting to his reprehensible road rage.Sign up for our Newsletter: https://thetransaction.substack.com/Critical TakeawaysFor the love of god, please prioritize quality ahead of quantity. For example, your sales and marketing teams should focus on producing high-quality content and interactions that resonate with target customers, rather than just attempting to increase touchpoints indiscriminately. Just because you can, definitely does not mean that you should (You should have learned this from Jurassic Park).Publishing quality content consistently is critical for anyone building a following on social media platforms. A good cadence for growth on most platforms is posting three times a week. This helps you stay on top of your audience’s feed and top of mind for buyers.Create content in the medium and format that is most comfortable for you. Whether it’s writing, video, or audio, the point is to not make the content production process more painful for you.The three types of stories that Scott recommends founders telling are: 1. How well you understand customer pain points, their priorities, and how to solve their problem. 2. How the market will change and how to navigate it. 3. Your personal journey.Using AI to write crappy, clearly fake comments on LinkedIn posts from contacts within your target accounts will cause major damage to your brand. Automated comments on LinkedIn are extremely easy to spot and Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Walking Through a Winter Wonderland03:23 - Introducing Scott Albro10:51 - AI Adoption is Taking Us Down the Wrong Path13:20 - The Important AI Debates Happening Today16:03 - Where AI Agents & Co-Pilots Fit into Go-To-Market27:20 - Using AI on LinkedIn37:47 - Creating Quality Content47:29 - Scott's Framework for Which Story Founders Want To Tell50:22 - Examples of The Best Founder Brands57:21 - The Impact of Scott's Shoe Game on the MarketEpic Quotes“ AI feels like a market where we are going to experiment our way into the right use cases. Because they're not obvious” - Scott Albro“Every founder has a story to tell. Otherwise they wouldn't have started a company.” - Scott AlbroConnect with Scott AlbroLinkedIn: https://www.linkedin.com/in/scottalbro/  ShoutoutsChris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris Orlob’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-143505807?utm_source=notes-share-action&r=3iae7zMatt Dixon: https://www.linkedin.com/in/mattdixon/ Matt Dixon’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-153859244?utm_source=notes-share-action&r=3iae7zDavid Politis: https://www.linkedin.com/in/davidpolitis/ David Politis’ Episode of The Transaction: https://substack.com/@thetransaction/note/p-152597131?utm_source=notes-share-action&r=3iae7zJohn M. Jack: https://www.linkedin.com/in/johnmjack/ Bland.ai: https://www.bland.ai/ Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan Gottlieb’s episode of The Transaction: https://substack.com/@thetransaction/note/p-149757433?utm_source=notes-share-action&r=3iae7zGartner: https://www.gartner.com/en AI Adoption Study from Scale Venture Partners: https://www.scalevp.com/insights/ai-gtm-flash-survey-how-marketing-teams-are-actually-using-ai/ Regie.ai: https://www.regie.ai/ Outreach: https://www.outreach.io/ Salesloft: https://www.salesloft.com/  Srinath Sridhar: https://www.linkedin.com/in/sridharsrinath/ Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Marc Beniof: https://www.linkedin.com/in/marcbenioff/ Tobias Lütke: https://www.linkedin.com/in/tobiaslutke/ Shopify: https://www.shopify.com/ ServiceTitan: https://www.servicetitan.com/ Adam Robinson: https://www.linkedin.com/in/retentionadam/ RB2B: https://www.rb2b.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/  Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

What is your GTM strategy built on? The cool new motion that's popular this minute? Tons of research on users? Well, it should be built from a blueprint and this guest just so happens to know how to create said blueprint. Adam B. Needles, the CEO of ANNUITAS, joins Craig Rosenberg and Matt Amundson for a barn burner of an episode that starts off with Adam’s seriously spicy take that the CMO’s role is a major part of the problem in the current B2B buying experience (Sounds like someone got into the Commsor hot sauces). After unpacking that hot tamale, Adam shares some great insights on the three parts to setting up and monitoring your Go-To-Market Blueprint, why you need to educate your board on how you go to market, and what buyers actually want from sellers during their buying journey. As if that wasn’t enough to include in this edition, Adam also drops a great nugget that AI can’t cover up your poor GTM Strategy. Pretty sure the B. in Adam’s name stands for B2B Badass or something like that based on this episode. (Yes, that was corny and stupid and yes, a human, albeit not a very bright one, wrote that)Also, Craig reminisces about his viral, rebellious past and Matt sits in a corner and cries at the downfall of his fiefdom.Critical TakeawaysThe three core components of a go-to-market blueprint are understanding the buyer's journey, identifying all relevant decision-making stakeholders, and grasping their content consumption habits. This helps in synchronizing b2b marketing and sales efforts to ensure value-added interactions at every touchpoint.Every b2b marketing touchpoint should focus on adding value to the prospect's journey. That means every email, meeting, and piece of content prospects receive serves a purpose and helps them arrive at a quality decision faster.Don’t treat your go-to-market plan as if it’s set in stone. You should regularly meet with crossfunctional leaders to review the gtm blueprint, examine your performance against that blueprint, and update your go to market strategy based on new data and insights. Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Freeing The Funnelholic07:18 - The Problematic Role of the Chief Marketing Officer for B2B companies20:52 - Creating a Value-Added Demand Motion for Buyers34:11 - Building Your Go-To-Market Blueprint40:47 - How to Get Your Board… On Board49:53 - Daring to Peek Outside of the Tech Industry56:17 - Your B2B Go-To-Market Playbook Needs a PlaybookSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ I don't think that AI is the solution to your bad go to market.” - Adam B. Needles“It's not about funnel management. It's really about just understanding where someone is in the journey.” - Adam B. Needles“If you don't have a clear sense of who owns what by stage, then nobody owns it.” - Adam B. Needles“ The new playbook is to have a playbook.” - Matt Amundson“ We talked about the CEO and COO, actually, now, the biggest education point for this change is board level.” - Craig RosenbergConnect with AdamLinkedIn: https://www.linkedin.com/in/abneedles/ Website: https://www.annuitas.com/ ShoutoutsCarlos Hidalgo: https://www.linkedin.com/in/carlosahidalgo/ Jason Stewart: https://www.linkedin.com/in/jasonhstewart/ MonotypeNinan Chacko: https://www.linkedin.com/in/ninan-chacko-54b527/ Bob Seiler: https://www.linkedin.com/in/robertjseiler/ Schneider ElectricProcter and GambleQA SymphonyForresterGartnerEvan Kent: https://www.linkedin.com/in/evankent/ SalesloftOutreachHubSpotLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

If people are the ones buying software, then it’s probably important that your brand appeals to those people.Fresh off a successful Dreamforce, Mini Peiris, the Chief Market Officer of Nintex, joins co-hosts Craig Rosenberg and Matt Amundson for an examination of how a brand should make buyers feel about themselves, the problems they face, and the solution provided. Mini also gets into when is the best time to ask customers for referrals, why playing nice with sales is key to being a successful Chief Marketing Officer, and how to reinforce a brand internally so that every customer touchpoint and interaction feels right. In a seeming first for the show, the conversation takes us past the point of transaction to look at the CMO’s role in the customer’s post-sale experience.Also, Craig reveals his favorite source of apple fritters and Matt says something that is very succinct and to the point.Critical TakeawaysEven though you’re in B2B, it's still humans making the purchasing decisions. Focus on the people behind the accounts, the problems they face, and what their goals are to create more impactful B2B marketing messaging.Marketing’s job isn’t over when the customer signs on the line which is dotted. It’s crucial to continue engaging with customers post-transaction to ensure they derive value from your product and can become powerful and vocal advocates of your brand.The CEO is critical in developing and or pivoting the internal brand and culture of a company. Understanding them and getting their buy in and support is step number one for any Chief Marketing Officer looking to establish or adjust their company's brand.Great B2B marketing and storytelling can gloss over a product’s inferiorities and position a brand as the category leader. If you can articulate the customers’ problem and your solution better than your competitors, your brand will win, giving you time and resources to then shore up product deficiencies. Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 - Live from San Fran, It’s Matturday Night Live04:10 - What Makes a Great CMO and B2B marketing leader07:34 - Don’t Forget that People Buy Software in B2B13:38 - How Mini Built a Customer Community with Donuts18:57 - Developing Your B2B Brand’s Core Identity21:59 - The CEO’s Influence on Brand & Culture 27:19 - Examples of Great B2B Brands32:34 - The CMO’s Role in The Post-Transaction Customer Experience40:19 - How Execs Buy B2B Software Today: Friends over FunnelsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“You have to know yourself before you can go tell others your story.” - Mini Peiris“ Nobody buys anything these days without calling up three of their friends. So if a friend's already making the intro, cause they took the leap, you have a better shot.” - Mini PeirisConnect with MiniLinkedIn: https://www.linkedin.com/in/mini8ture/ Website: https://www.nintex.com/ ShoutoutsMatthew Luhn: https://www.linkedin.com/in/matthew-luhn-52a40629/ Geraldine McGinty: https://www.linkedin.com/in/geraldinemcgintymd/ Drift: https://www.salesloft.com/platform/drift HubSpot: https://www.salesloft.com/platform/drift Zendesk: https://www.zendesk.com/ Rippling: https://www.rippling.com/ Lifetime Fitness: https://www.linkedin.com/company/lifetimeinc/ Qualtrics: https://www.qualtrics.com/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

What would you say if your CEO told you they wanted to speak with 100 customers in 100 days? That’s exactly what our guest, David Politis, did and he still thinks it’s one of the best things he’s done in his career.David, the Founder and Executive Chairman of BetterCloud and Host of Not Another CEO Podcast, joins co-hosts Craig Rosenberg and Matt Amundson for a must-listen episode for founders, CEOs, and B2B execs. David explains why having a smaller TAM (Total Addressable Market) is actually good for smaller or newer-stage companies. There are also great discussions about when landing a big customer can be a bad thing for your company’s roadmap, why meeting with customers is so critically important for leaders, and how to stand out as a sales rep to book meetings with decision-makers at ideal customers.Also, Matt gets a very meaningful head nod and Craig is called an inspiration, a high that his ego may be chasing for a long time.Critical TakeawaysNarrow down both your ideal customer profile and your ideal buyer persona. While this may seem counterintuitive, the larger your TAM (Total Addressable Market), the slower your company will grow. When you try to go after too many customer profiles and buyer personas, your budget, time, and effort get dispersed across them and it’s harder to gain a real foothold in any niche from which you can later expand beyond.When you focus on one key buyer persona within one ICP (Ideal Customer Profile), you can delve deeper into understanding not only how they will use your product, but also what your product actually means to them. For example, when Matt was working in marketing automation, he was able to understand that his product gave buyers a seat at the revenue table and made their jobs easier.Especially for early-stage startups, there is nothing that is more valuable than talking with your customers. Those conversations function as critical data points that you can use in every aspect of the company, from writing messaging and crafting sales narratives to building new features and raising funds. Proving to people that you and your email or message aren’t just automated is harder than ever now, so to really cut through the noise and get noticed, you need to do things that can’t be automated. In-person and handwritten things work well for this.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 When Craig Met David, His Forever-23-ish Wunderkind06:07 Stop Supersizing Your TAM, Narrow Down Your ICP09:34 The Dangers of Landing a Whale Client & How To Handle Your Big Fish18:11 Which Comes First, The Product or The Persona?23:19 Why a CEO Would Want to Meet 100 Customers in 100 Days30:48 Sales Reps Need To Take The Opposite Approach to Automation41:50 Creating Memorable Moments for Prospects & Customers Through Events47:50 Matt Provides His Expert Critique of David’s Art ExhibitionSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“In the early stage, every customer conversation is gold.” - David Politis“There's nothing that you can do that's as valuable as meeting customers, once you're an executive.” - Matt AmundsonConnect with DavidLinkedIn: https://www.linkedin.com/in/davidpolitis/ BetterCloud Website: https://www.bettercloud.com/ Work-Bench Website: https://www.work-bench.com/ Not Another CEO Podcast: https://podcast.notanotherceo.com/ The StartUp Founder Survival Guide: https://www.linkedin.com/posts/davidpolitis_startup-founder-survival-guide-david-politis-activity-7158455968194875393-QVdh ShoutoutsChris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Ryan Azus: https://www.linkedin.com/in/ryanazus/ Megan Eisenberg: https://www.linkedin.com/in/meageneisenberg/ Warburg Pincus: https://warburgpincus.com/Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

How do you steal the spotlight from Marc Benioff at Dreamforce? By hiring a Benioff impersonator. Yes, Kyle Porter and the Salesloft team ACTUALLY did that. But they didn’t stop there…Joining co-hosts Matt Amundson and Craig Rosenberg to chat about the amazing stunts pulled in the early days of Salesloft and how to build a healthy company culture is Kyle Porter himself, the Founder and Board Chair of Salesloft. Beyond bringing a Benioff doppelganger to Dreamforce, Kyle shares some brilliant plays his team used to drive brand awareness and become the biggest story at their competitor’s conference. Kyle also dives into how he built a loving culture within Salesloft and how that loving culture was extended to and felt by their customers. Also, Craig provides a gripping tale about his experience with an elevator and Matt sets the record straight on whether a presentation he gave was sweaty or swear-y.Sign up for our Newsletter: https://thetransaction.substack.com/Critical TakeawaysWhen you really love your customers and they can actually feel that love, they are willing to go to bat for you and your company. Because Matt felt that Kyle loved him-as a customer-he would defend and promote Salesloft when others were defending or promoting a competitor.Building a strong company culture is more important than ever. It should be built on love–in a platonic way–for the members of your organization. A healthy organizational culture translates to better team dynamics, productivity, and ultimately, better customer interactions and satisfaction.Dare to be different, especially when it comes to events. People will only really remember 1-2 things from an event, so it’s critical to make that shortlist. A bigger booth doesn’t necessarily make you more memorable. Most event booths zig, so find a way to zag, even if it means doing something other than a booth (Sorry if that one hit too close to home).Sponsored SegmentThis episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com.Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Introducing Kyle Porter!08:25 Awesome SaaS Stunts from the Salesloft Team26:00 The Importance of Organizational Culture and Leadership30:18 Loving Your Customers32:54 Building a Community & Leveraging Customer Advocacy44:28 How to Build a GREAT Sales Deck and Engage with Key Decision Makers50:36 The Impact of Kyle’s Brand as a FounderEpic Quotes“We're going to continually love and serve our customers and our people better than anyone else. And when you care more than anyone else, you're going to win ultimately.” - Kyle Porter“When a customer bought SalesLoft, I had the mentality that they had just saved my life and I was going to treat them as such” - Kyle Porter“Taking care of your employees Actually helps you take care of your customers” - Matt AmundsonConnect with KyleLinkedIn: https://www.linkedin.com/in/kyleporter/ Website: https://www.salesloft.com/ Kyle’s post about the Marc Benioff Impersonation (with pictures): https://www.linkedin.com/pulse/20141022175506-2446560-how-we-impersonated-the-salesforce-com-ceo-for-one-of-the-best-marketing-hacks-at-dreamforce/ The Puppy Party for #Unleash17: https://x.com/Salesloft/status/872167164123459584 ShoutoutsJon Birdsong: https://www.linkedin.com/in/birdsong/ Mike Damphousse: https://www.linkedin.com/in/damphoux/ Behind the Cloud by Marc Benioff: https://amzn.to/3CE8WXS AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ AJ Gandhi’s episode of The Transaction: https://thetransactionpod.com/episodes/navigating-market-success-with-aj-gandhi-the-transaction-ep-26 Cam Melson: https://www.linkedin.com/in/cameronmelson/ Anthony Zhang: https://www.linkedin.com/in/theanthonyzhang/ Tami McQueen: https://www.linkedin.com/in/tamimcqueen/ Business Insider Article about Benioff for President Campaign: https://www.businessinsider.com/dreamforce-2015-adrian-grenier-wants-to-be-marc-benioffs-running-mate-2015-9 Sean Kester: https://www.linkedin.com/in/theseankester/ Mac Reddin: https://www.linkedin.com/in/mac-reddin/ Kevin O’Malley: https://www.linkedin.com/in/omalley/ Peter Kazanjy: https://www.linkedin.com/in/kazanjy/ Carolyn Feibleman: https://www.linkedin.com/in/carolynfeibleman/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ Steve Richard: https://www.linkedin.com/in/saleskickoffspeaker/ John Barrows: https://www.linkedin.com/in/johnbarrows/ Jason M. Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Mark Suster: https://www.linkedin.com/in/marksuster/ Brad Feld: https://www.linkedin.com/in/bfeld/ Ken Krogue: https://www.linkedin.com/in/kenkrogue/ Love the show? Give us a shoutout on LinkedIn and tell what you loved!

What does a sales opportunity mean to you? Would the rest of your company give the same answer? Probably not. But not to fear, GTM leader, because Tricia Gellman, the Chief Marketing Officer of Box joins hosts Matt Amundson and Craig Rosenberg to explain how to fix the cracks between sales and marketing in B2B. Tricia outlines the importance of having shared goals across B2B sales and marketing teams, why defining terms clearly is so critical, and what it’s like for those selling AI tools to B2B buyers.Also, Craig recounts his time spent hanging out with reps at Dreamforce and Matt gushes about the events TOPO used to run.Critical TakeawaysA crucial component in driving B2B sales and marketing alignment is using the same metrics and dashboards to accomplish shared goals. Consistency and agreement on these metrics will help streamline the goal-setting process, reduce friction, and ensure everyone is working towards the same company objectives.Clearly define what constitutes an opportunity and different stages within the pipeline. Aligning these definitions across marketing and sales will prevent discrepancies and confusion, leading to more accurate performance tracking and reporting.Invest in brand building. A strong B2B brand is essential for long-term success and helps in making conversations happen at the C-suite level. This investment continues to pay off by fostering word-of-mouth recommendations and creating a lasting impression in the minds of decision-makers.Building a customer or peer community, especially around high-level executives and key decision-makers, can significantly enhance your brand's reach and credibility. Hosting events and creating opportunities for peer networking add tremendous value and deepen customer loyalty.Sponsored SegmentThis episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com.Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Tricia's Italy Trip & Career Advice03:08 Overcoming the Challenges of a B2B Chief Marketing Officer04:51 Managing Pipeline in the Current SaaS Environment08:56 How to Align B2B Marketing and Sales Teams23:26 Aligning Incentives Across Go-To-Market Teams24:01 Defining Opportunities and Meetings25:18 Adapting to AI in B2B Sales27:13 Transitioning to a New CMO Role in a B2B company32:22 Building a Customer Community and Product AlignmentSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Saying you can't do it because you don't have the data is just a cop out.” - Tricia Gellman“Everybody works to their goals. Whatever the incentive is, that's what people work towards.” - Tricia Gellman “One of the key roles of leadership across sales and marketing is really being clear on who are we going after? Why are we going after it? And then, how are we going to go after it?” - Tricia GellmanConnect with Tricia GellmanLinkedIn: https://www.linkedin.com/in/gellmansfmarketing/ Website: https://www.box.com/home ShoutoutsMini Peiris: https://www.linkedin.com/in/mini8ture/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Latané Conant: https://www.linkedin.com/in/latane-conant/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Wow, Season Two is kicking off strong with this incredible episode with Dave Gerhardt, an astonishing marketer and the Founder & CEO of Exit Five. Dave joins Craig Rosenberg and Matt Amundson to share how he approaches using AI for B2B marketing, why LinkedIn influencers present a huge opportunity for B2B brands, and the outsized impact that building a strong Founder Brand can have for startups. Also, Matt shares his innermost feelings about Dave and Craig examines his own facial hair.Critical TakeawaysSocial media should be treated as the primary marketing channel for B2B SaaS brands, not just a supplementary piece of your strategy.AI tools are best used as an “idea starter” to get your writing going, rather than relying on the artificial intelligence to do the actual writing itself.Working with micro-influencers who have a strong, niche following can be highly effective in B2B SaaS. To see good results, it's important to create offers and content that align with what their audience wants to see. Narrowing down your Ideal Customer Profile (ICP) is crucial for B2B growth. Starting with a more specific market allows for easier traction and learning which you can later apply more broadly as your company scales. Sponsored SegmentNew Sponsor coming soon!Interested in becoming a sponsor of The Transaction? Contact [email protected]:00 Matt provides a safe space for Dave02:06 Discussing Founder Brand and B2B Marketing Strategies04:45 The Power of Personal Branding and Social Media for Startups09:42 AI Tools in B2B Marketing: Opportunities and Misconceptions20:00 B2B Influencers and LinkedIn Strategies for SaaS companies26:19 Understanding the Full Funnel in B2B Marketing27:26 The Power of LinkedIn and Social Media31:18 Narrowing Down Your Ideal Customer Profile (ICP)37:03 The Story Behind Drift's Success40:00 Building a Strong B2B Brand and Content Strategy46:56 An In-depth Review of Craig’s Facial HairSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Social media is the way marketing happens in our lives today.” - Dave Gerhardt“I use [AI] a lot as my writing partner, you can't really have writer's block anymore because you kind of always have something to get going” - Dave Gerhardt“I love you.” - Matt AmundsonConnect with DaveLinkedIn: https://www.linkedin.com/in/davegerhardt/ Website: https://www.exitfive.com/ Podcast: https://media.exitfive.com/podcast ShoutoutsAdam Robinson: https://www.linkedin.com/in/retentionadam/ Bland AI: https://www.bland.ai/ HeyGen: https://www.heygen.com/ Danielle Messler: https://www.linkedin.com/in/daniellemessler/ Natalie Taylor: https://www.linkedin.com/in/nataliecstaylor/ Capsule: https://capsule.video/ Planful: https://planful.com/ Mac Reddin: https://www.linkedin.com/in/mac-reddin/ David Politis: https://www.linkedin.com/in/davidpolitis/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Today Matt and Craig open the floodgates to actionable marketing insights with seasoned guest, Carlos Hidalgo Co-Founder and CEO of Digital Exhaust. The episode focuses on the landscape of marketing, shedding light on the challenges and missteps related to AI, new technologies, and the tendency to chase after shiny objects. It examines the struggles CMOs face in balancing short-term demands with long-term strategies, emphasizing the significance of mutual respect and alignment between marketing, sales, finance, and product teams for sustainable success. Takeaways:Treat sales, finance, and product teams as partners. Spend dedicated time to understand their perspectives and needs, just as you would with external customers.Avoid reliance on broad ICP (Ideal Customer Profile) definitions. Instead, invest in detailed customer insights and keep them updated.Encourage shared goals amongst all business teams to foster a sense of joint accountability and drive consistent messaging and strategy.Resist the temptation to engage in short-term tactics at the expense of long-term strategy. Balance immediate actions with initiatives that build sustainable growth.Use customer insights to drive the creation of valuable content, campaigns, and product features that genuinely address customer pain points.Integrate sales feedback into marketing plans to ensure campaigns and content meet the practical needs of the sales process.Celebrate joint successes and publicly acknowledge contributions from different teams to reinforce the value of teamwork.Chapters:00:00 Introduction / Why Are You Bitter Today?02:08 Guest Introduction: Carlos Hidalgo02:30 Carlos' Story: Meeting Craig07:54 Market Misconceptions and Shiny Object Syndrome08:57 The Importance of Customer Understanding10:38 CMOs and the Seat at the Table18:09 Alignment Across the Organization25:58 Shared Goals and Compensation27:47 Customer-Centric Marketing28:18 Addressing Sales Roadblocks32:41 The People Problem in Alignment35:39 The Role of Marketing in Sales Success38:10 Understanding the Customer42:13 Final Thoughts and ConclusionQuote of the Show:“Growth doesn't go out of style. Growth has always been the goal.” - Carlos HidalgoSponsor:The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Connect with Carlos:LinkedIn: https://www.linkedin.com/in/carlosahidalgo/ Website: https://digitalexhaust.co/ Shoutouts:Phil Fernandez https://www.linkedin.com/in/phil-fernandez-6902881/ Ray Rike https://www.linkedin.com/in/rayrike/ AJ Gandhi https://www.linkedin.com/in/anjaigandhi/ McAfee https://www.mcafee.com/ ZoomInfo https://www.zoominfo.com/  Follow the Show:Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1