The GTMnow Podcast

Boomi was founded in the early 2000s by Rick Nucci, acquired by Dell in 2010, and then spun out to Francisco Partners and TPG Capital in 2021. Today it powers 30,000+ enterprise customers globally and moves more data per second than the entire Visa card network, times two. What started as an integration platform has evolved into something bigger: the leading data activation company, purpose-built for the agentic AI era.Steve Lucas took over as CEO in early 2023, just as ChatGPT was about to reshape the entire software landscape. A three-time CEO with nearly 30 years in enterprise software, Steve previously led Marketo through its $4.75B acquisition by Adobe (the largest in Adobe's history at the time), scaled iCIMS into the world's leading talent acquisition cloud, and held senior roles at SAP, Salesforce, Adobe, and BusinessObjects. He's also the author of "Digital Impact: The Human Element of AI Driven Transformation," a book arguing that the AI revolution will stall unless companies fix the fragmentation of their data first.In this episode, Sophie Buonassisi sits down with Steve at HumanX in San Francisco to unpack why 2026 is the year AI moves from pilot to production, the three diagnostic questions every CEO should ask before deploying agentic AI, and why "change only happens at the speed of trust." Steve also gets candid about the internal protest that erupted when Boomi rolled out its first CSM agent, his prediction that AI will go from influencing 20% of executive decisions to making 90% of them within 2 years, and how he picked up Claude Code on an airplane to vibe-code a contracts agent for his sales team.If you're a founder, operator, or GTM leader trying to figure out whether your business is actually ready for agentic AI (or just chasing the buzzword), this one is for you.TIMESTAMPS0:00  Intro0:58  Welcome to GTMnow at HumanX1:10  Why 2026 is when AI moves from pilot to production2:32  Influencing decisions vs. making decisions: the next 2 years3:18  Digital Impact: why fragmentation will stall the AI revolution5:01  "Get your data to the gym": the new slogan5:20  The 3 questions to know if your company is AI-ready6:47  Change happens at the speed of trust7:53  The internal protest behind Boomi's CSM agent9:32  From integration platform to data activation: the strategic shift10:50 Steve's most transformative AI workflow as a CEO11:12 Vibe coding with Claude on an airplane12:20 Where to follow Steve and BoomiHost: Sophie Buonassisi, SVP Marketing at GTMnowlinkedin.com/in/sophiebuonassisi  Guest: Steve Lucas, CEO at Boomihttps://www.linkedin.com/in/nstevenlucas/Visit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/Sponsors: .Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.comFor inquiries about sponsoring the podcast, email gtmnow@gtmThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target.From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround stories in enterprise SaaS. In this episode, Jon pulls back the curtain on exactly how it happened.In this episode:- Why 91% of enterprises are already deploying AI agents but only 10% have a security strategy for them- How Okta's "AI governance gap" insight became the foundation for their biggest product launch in years: Okta for AI Agents- The GTM restructure around specialization that unlocked productivity and drove 40% higher average contract value on new product deals- How Okta became a partner-first company: 95% of their top 100 deals in the last fiscal year were partner-led, and what operationally made that possible- Why the first discovery call no longer exists, and how sellers need to show up differently in the AI era- Jon's new internal sales methodology, APEX, built on Command of the Message for the AI era- How Okta is using AI internally to transform their own go-to-market motion, from conversational intelligence to pre-sales assistants- What the path to $5B ARR actually looks like: enterprise expansion, international growth, public sector, and the massive new TAM unlocked by non-human identity- Jon's leadership philosophy: why human-centric selling is becoming more critical as AI takes over the repetitive workHost: Sophie Buonassisi, SVP Marketing at GTMnowhttps://www.linkedin.com/in/sophiebuonassisiGuest: Jon Addison, CRO at Oktahttps://www.linkedin.com/in/jon-addison-3399175Timestamp:0:00 - Cold open1:19 - Welcome + Jon's background: from London to Silicon Valley1:52 - How Jon got into software and identity management4:08 - Okta for AI Agents launch announcement5:04 - 90% of customers live with agents, only 10% confident in securing them6:31 - What's driving the governance gap in the market7:53 - Speed of agent innovation must be matched by security and governance8:36 - 40% higher ACV on deals that include new products9:43 - Why consolidation around a single identity platform is resonating11:45 - How AI agents unlock a massive new TAM for Okta13:05 - Okta's turnaround: from $850M operating losses to $760M operating income13:36 - Key decision 1: GTM specialization drove productivity15:02 - Key decision 2: becoming a partner-first company16:14 - What cracking the partner-led model actually looks like19:08 - How long it takes to see ROI from a partner-led pivot20:12 - The path from $3B to $5B: enterprise, international, public sector21:49 - Using AI internally: launching "Apex," the AI-era sales methodology23:04 - What the Apex sales methodology entails24:25 - Buyers now show up with strong opinions before the first call25:44 - How discovery is changing: human-centric selling in the AI era27:33 - Headcount and AI: what skills matter in the future29:31 - Why relationships are Okta's core competitive advantage30:36 - The role of experiences: F1, events, and the 7-touchpoint rule31:47 - Broad GTM surface area: ABM, ecosysThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next.Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else did, what makes a founder worth backing regardless of the tech, and why the next wave of AI infrastructure is being rebuilt from the ground up.In this episode:- Why a16z bet $1.7B on AI infrastructure (and why now)- The shift from cloud to AI-native infrastructure: storage, compute, orchestration, memory- How ElevenLabs crossed the uncanny valley in synthetic voice- Voice agents as the first AI category to truly scale in the enterprise- What "king-making" in AI go-to-market actually looks like- The traits that made Jennifer write a check for ElevenLabs on founder conviction alone- Open source vs. frontier models: what 2027 looks like- Why world models and vision language models are the next unlock- AI and human creativity: why directors and authors won't be replaced- How a 1-2 person studio can now make a full movieHost: Sophie Buonassisi, SVP Marketing at GTMnowhttps://www.linkedin.com/in/sophiebuonassisiGuest: Jennifer Li, General Partner at Andreessen Horowitzhttps://www.linkedin.com/in/jenniferhli/https://x.com/JenniferHliConnect with Max: https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschulerConnect with Paul:https://x.com/PaulGTMhttps://www.linkedin.com/in/paulsirvingTimestamps:0:00 - Cold open1:06 - Max & Paul intro: are we in a bubble?1:46 - AI vs. dot-com era: the key differences4:55 - B2B SaaS disruption and value destruction (Thoma Bravo / Medallia)6:39 - Intercom / Finn: crossing the chasm from legacy to AI-native8:08 - Introducing Jennifer Lee, a16z General Partner8:31 - Paul's key takeaway: the distribution era9:41 - Why speed to default brand has never mattered more11:33 - The ElevenLabs story: a16z led Series A, B, and C12:02 - Why the seed strategy still works13:37 - What the best founders do differently with model capabilities15:58 - Jennifer Lee joins: why a16z raised $1.7B for infrastructure16:22 - What existing infrastructure is being rebuilt for AI19:19 - Specific areas a16z is focused on: models, storage, dev tools, security20:35 - 90%+ of code now written by agents21:52 - What Jennifer saw early in the 11 Labs / voice AI space25:19 - Go-to-market in AI infrastructure: what's working27:29 - Becoming the default brand: the "Kleenex effect" in AI28:37 - What makes a founder worth backing on conviction alone30:48 - Predictions for 2026/2027: open source catching up fast31:39 - Most exciting new modalities: world models and vision language models32:07 - AI and human creativity: can they coexist?34:42 - What's blocking the creative AI future36:05 - "The best ideas live in the graveyard"36:57 - Closing advice: make AI tools your friendsVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG). But the path there was anything but smooth.In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.We cover:- Why Figma refused to discount, even when Microsoft pushed back- How to hire the right first sales rep as a founder- The PLG to enterprise transition most companies get wrong- What the Adobe deal collapse actually felt like from the inside- How Figma went from 3 products to 8 overnight and launched into an IPO- What great sales look like in the AI eraTimestamp:0:00 – Intro 1:02 – Guest intro: Kyle Parrish 1:35 – Joining Figma at $2M ARR in 2018 5:01 – First meeting with Dylan (Figma CEO) 6:13 – How to find your first sales hire 9:05 – Stage alignment in early hiring 11:43 – Early-stage operators need "scar tissue" 13:19 – Northstar metric at Figma 14:13 – Obsessing over customer conversations 16:44 – Building Figma's brand through community 17:31 – Scaling the "unscalable" 20:08 – In-person GTM vs. digital 22:47 – Was there a moment Figma might not make it? 24:48 – Pivoting after the Adobe deal collapsed 28:10 – Figma's no-discount rule 31:05 – Enterprise ELAs replacing discounting 34:47 – What makes a great salesperson in the AI era 36:56 – Missionaries vs. mercenaries in AI-era GTM 39:47 – Spotting the next Dropbox or Figma 43:46 – Kyle's post-Figma investing focus 45:58 – Family, travel & what's nextGuest: Kyle Parrish, former VP Sales at Figma LinkedIn: https://www.linkedin.com/in/kparrish8/X: https://x.com/KyleHParrishHost: Sophie Buonassisi, SVP Marketing at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/Sponsors: Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.comFor inquiries about sponsoring the podcast, email [email protected] is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/The GTMnow PodcastThe GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other intereThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.Sam, Founder and CEO of TestBox, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.What we cover:Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)The shift from discovery calls to validation calls, and how to prepareCEO (AI-version of SEO): how LLMs are shaping what buyers believe about your productThe "day one shortlist" shrinking from 3-4 vendors to 1-2 vendorsAgent-to-agent procurement: Sam's timeline for when AI agents fully take over buyingWhy the mid-funnel is actually getting longer, not shorterThe "Fake Nothing, Prove Everything" campaign that went viral post-Series AHow TestBox runs 15 AI experiments per week across the entire companyUsing Google Vertex video analysis to read prospect body language on sales callsHow to build an AI-first culture without burning out your teamBooks: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to GreatTimestamps:0:00 - Cold open1:09 - What TestBox does2:43 - How buying has changed5:48 - What founders/CROs should do now7:05 - GEO: AI version of SEO9:02 - Why mid-funnel is expanding21:17 - Agent-to-agent procurement26:02 - All procurement by agents in 3-5 years29:09 - How vendors differentiate beyond product33:30 - The croissant campaign breakdown45:50 - 15 AI experiments per week47:10 - Analyzing prospects via video AI48:29 - Building AI culture in your team52:39 - Book recommendationsGuest: Sam Senior, Founder and CEO TestBoxLinkedin: ⁠https://www.linkedin.com/in/samuelsenior/⁠TestBox:⁠ https://www.testbox.com⁠Host: Sophie Buonassisi, SVP Marketing at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter:⁠ https://thegtmnewsletter.substack.com⁠Visit us on:⁠ https://gtmnow.com⁠Follow us on LinkedIn: / gtmnowFollow us on X (Twitter):⁠ https://x.com/GTMnow_⁠ Follow us on YouTube: / @gtm_now Follow us on TikTok: / gtmnow_ Follow us on Instagram: / gtmnow_  The GTMnow PodcastThe GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Auren Hoffman (Flex Capital) joins the GTMnow podcast to share some of the most contrarian takes in tech today, from why AI moats are gone, to why your next VC meeting will be with a bot, to why AI is secretly going to trigger a baby boom.In this episode:- Why Auren runs 500+ AI agents to source deals, and what that means for founders raising capital- The "agent-to-agent" meeting prediction: by end of 2026, first VC conversations will be fully automated- Why every software moat has been "blown up" and what Salesforce, LinkedIn & DocuSign need to do to survive- The OpenAI x The Hustle acquisition breakdown: why it's the smartest (and cheapest) distribution play in AI- Why missing a great deal is 10x more painful than making a bad one, Auren's honest VC mistake framework- The baby boom thesis: why AI, IVF, self-driving cars & cheaper energy could reverse the fertility decline- Why companies won't sign yearly SaaS contracts anymore, and what that means for every B2B founderAuren Hoffman is the founder of Flex Capital, SafeGraph, and LiveRamp. He's an early backer of Replit, Perplexity, Rippling, Vercel, Coinbase, Chime, and AppLovin.Connect with Max: https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschulerConnect with Auren:https://x.com/aurenhttps://www.linkedin.com/in/auren/https://www.youtube.com/@summationpodGTMnow shares how the best in tech build, scale and invest.Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.GTMnow is run by GTMfund - we are an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.Chapters:00:00 - Intro01:05 - GTMfund Q1 recap 02:38 - OpenAI x The Hustle breakdown 06:18 - Redpoint's optimal VC deployment period 11:24 - Auren Hoffman intro 13:04 - Why am I seeing this deal? 26:26 - Sizing up founders at Replit, Perplexity & Rippling 28:49 - What separates great founders 32:10 - 500+ AI agents for deal sourcing 33:40 - Agent-to-agent VC meetings by 2026 45:13 - Every software moat is blown up 49:09 - Who kills Salesforce next? 51:30 - Why no one signs yearly SaaS contracts anymore 51:50 - AI will trigger a baby boom 56:22 - Thinking generationally#AI #VentureCapital #GTM #StartupFunding #AurenHoffman #FlexCapital #SaaS #ArtificialIntelligence #Founders #SalesVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Wade Foster is the CEO of Zapier, a company that sits between 7,000+ apps and runs millions of automations every single day. That gives him a front-row seat to how companies are actually adopting AI, not just talking about it.In this episode, Wade breaks down the exact decisions he made at Zapier to go from 10% AI usage to 97% company-wide, why agents and workflows are not the same thing, and what most leaders are getting completely wrong about AI fluency.What you'll learn:The difference between agents and workflows (and when to use which)What triggered Zapier's internal "Code Red" after GPT-4 launchedThe one-week hackathon that took AI adoption from 10% to 50% overnightThe AI fluency rubric Zapier built: Unacceptable, Acceptable, Adaptive, TransformativeWhy leaders who aren't using AI are the biggest bottleneck in their companiesHow to measure AI ROI: floor raisers vs ceiling raisersHow AI now handles 50% of Zapier's customer support ticketsWade's personal "advisory council" of AI sub-agents he uses for every major decisionWhy building a company today is 10x cheaper but distribution is 10x harderThe truth about fundraising: you're selling your company, not raising moneyHow Zapier stayed profitable by only hiring when it hurtGuest: Wade Foster, CEO of Zapier LinkedIn: https://www.linkedin.com/in/wadefoster/Company - Zapier: https://zapier.comHost: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://thegtmnewsletter.substack.comEpisode highlights0:00 - Intro1:13 - The Seinfeld Quote & Kanye Text story3:16 - Workflows vs. Agents: What's the difference?6:09 - Zapier's Code Red moment8:55 - The hackathon that moved AI adoption from 10% to 50%12:06 - Making AI fluency a hiring requirement13:47 - Building the AI fluency rubric16:40 - Why leaders are the biggest AI bottleneck18:12 - Revenue impact of going AI-first22:09 - Would Wade build Zapier differently today?23:20 - Is Zapier's moat at risk from agents?24:59 - Staying profitable with minimal capital28:37 - The riskiest contrarian bet that paid off31:52 - Wade's 3 personal AI workflows36:53 - Favorite books for foundersGTMnow is the media brand of GTMfund, sharing go-to-market insights from working with hundreds of portfolio companies backed by 350+ of the best GTM executives. Subscribe for weekly episodes with the operators, founders, and investors behind the fastest-growing software companies.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Ed Sim has been a VC for 30 years. He's backed companies like Clay, Front, BigID, and Snyk. He writes What's Hot in Enterprise IT every single Saturday, 489 weeks in a row. And right now, he says this is the most exciting and terrifying moment he's ever seen in his career.In this episode, Max and Ed break down what's actually happening inside startups and boards right now, why the old playbooks are dead, and what separates the companies that will survive this AI shift from the ones quietly getting killed by it.Discussed in this episodeWhy engineering is no longer your bottleneck (and what is)The 5 P's Ed uses to evaluate every inception-stage investmentThe autonomous enterprise thesis and what it means for how companies are builtWhy AI-native leadership is now a survival reqxtuirement, not a nice to haveThe full Clay story: $600K to $100M ARR, how they stayed lean, and what actually unlocked growthThe 3 CH's framework for being a great board partner to foundersWhy the best founders today are inside the AI jet stream, not chasing itWhat every board meeting sounds like right nowEpisode highlights0:00 Intro & 1:05 Episode Preview: Ed Sim & Key Takeaways3:10 The Jet Stream Analogy: Two Types of Companies5:43 How GTM Operators Should Evaluate Companies Like Angel Investors7:20 The Collapsing of Moats & AI-Native Business Opportunities10:00 Rebuilding Industries vs. Selling Software to Them15:00 Why Old GTM Playbooks Are Dead17:46 Ed Sim's Background: From Cutco to 30 Years in VC21:43 The Five P's of Inception Investing23:04 How to Evaluate Potential & TAM in a Fast-Changing Market25:40 Staying Ahead of the Jet Stream as a Founder26:32 The Autonomous Enterprise Thesis28:44 Agent of the Week: How Companies Should Adopt AI Agents29:10 How Agents Are Changing Engineering Bottlenecks31:15 What Incumbents Must Do to Survive the AI Wave32:53 Intercom, Snowflake & How Legacy Companies Are Adapting36:43 The Clay Story: How They Found Their Footing38:33 The Three C's of Working With Founders (Cheer, Challenge, Chill)40:07 Clay's Growth Trajectory: $600K to $100M+ ARR41:10 Clay's Agency GTM Model & Community Moat43:50 Ed's Fund Model: $500K to $15M Checks at Inception46:57 What's Hot in Enterprise IT & Venture Right Now48:03 Closing RemarksKey takeaways1. Engineering is no longer your bottleneck. Your people are. Code is shipping faster than your sales, marketing, and customers can absorb it. The constraint has flipped completely and most companies haven't noticed yet.2. Painkillers beat vitamins every time. The only startups worth backing at inception are solving a hair-on-fire problem someone desperately needs fixed, not a nice-to-have they can live without.3. The 3 CH's of being a great board partner. Know when to Cheer (when founders are getting beaten up), when to Challenge (when they feel invincible), and when to Chill (when they just need breathing room to figure it out). Elliot used all three with Clay to perfection.4. If your CEO came from sales, you are in trouble. Surviving this AI shift requires product-driven, agent-native leadership at the top. The companies that adaptedThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the old reactive, relationship-based CS model is no longer cutting it.At Sophos, the threat landscape is compounding fast. AI is accelerating the speed and sophistication of attacks, which means response times, customer journeys, and success motions all have to evolve in lockstep in order to keep up. Teresa has spent her career at companies like Zendesk, Autodesk, and ON24 building the operational frameworks that make that possible at scale.Mentioned Resources: Cleverbridge: Merchant of Record for Software & SaaS​Guest links: Teresa Anania - LinkedIn: https://www.linkedin.com/in/teresa-anania/Sophos - LinkedIn: https://www.linkedin.com/company/sophos/Sophos - Website: https://www.sophos.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors: - HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/- Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, research, and sequencing so reps can focus on conversations. Learn more at The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Jason Demant just joined GTMfund as Partner, Head of Networks after 6 years at Foundation Capital where he reviewed over 1,000 emerging manager funds and invested in 100+.In this episode, Max (GP), Paul (GP), and Jason break down what separates the VC firms that survive from the ones that quietly die, why the best founders today are skipping mega funds at pre-seed, and what LPs are excited in about emerging managers.What we cover:The real reason raising from mega funds at pre-seed can backfireWhy less than 10% of VC firms ever make it to Fund 3What makes an emerging manager fundable (sourcing, founder support, durability)The media flywheel that gives certain funds an unfair advantageHow LPs should think about mega funds vs. emerging platforms (the barbell approach)Why founders are the ones now choosing their investors, not the other way aroundConnect with Jason:   / jasondemant   Connect with Max:   / maxaltschuler  Connect with Paul:   / paulsirving  GTMnow is the media extension of GTMfund, a venture capital firm investing in early-stage B2B companies. Every episode features operators, investors, and founders on the front lines of go-to-market.Timestamps:0:00 Intro1:54 Jason's Background at Foundation Capital3:07 Why Jason Chose GTMfund4:35 How Media Has Evolved in the VC Ecosystem6:20 What Separates Winning Emerging Managers from the Rest8:28 GTM Fund's Flywheel: Fund, Community & MediaThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

NEW: @Paul Fipps (President of Global Customer Operations at @ServiceNow) joins GTMnow to break down how ServiceNow built the customer engine behind $10B+ in revenue and 20%+ growth for five consecutive years.From CIO at Under Armour overseeing a 300 million-member connected fitness ecosystem, to now leading global sales, customer success, field marketing, and partners at one of the most disciplined GTM organizations in enterprise software, Paul has seen what it takes to scale from both sides of the table.In this conversation, you'll learn:- Why complacency is a bigger threat than competition at scale- How to detect churn long before it shows up in a report- What a CIO cancelling 900 AI pilots tells you about where enterprise AI is actually headed- How ServiceNow unified sales, customer success, field marketing, and partners into one GTM motion so customers never feel the org chart- Why ServiceNow monitors customer health daily — and what signals their teams actually track- How community became a core GTM advantage, not just a marketing channel- How ServiceNow’s AI Control Tower governs agents across the enterprise stack- Inside “Now on Now”: how ServiceNow generated $335M in annualized AI productivity gains using its own platform- How integrating Claude into the GTM workflow cut account planning from days to minutes- What DTC product thinking from Under Armour unlocked in enterprise GTM- How ServiceNow shifted from 6-month product releases to monthly innovation cycles- Paul’s advice for building a world-class GTM organization: put the best people in the right seatsGuest links: Guest - LinkedIn: https://www.linkedin.com/in/paulfipps/Guest company - LinkedIn: https://www.linkedin.com/company/servicenow/Guest company website: https://www.servicenow.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a generation of SaaS: enterprise segmentation, sales motion design, product marketing, the whole works. He then co-founded SmartRecruiters, angel invested in companies like Outreach and Pando, and eventually joined Bonfire Ventures as a Partner to do early-stage investing the way he thinks it should be done: hands-on, operator-led, and built around founders who are ruthless about execution.Guest links:Brett Queener - LinkedIn: https://www.linkedin.com/in/brettqueener/Bonfire Ventures - LinkedIn: https://www.linkedin.com/company/bonfire-ventures/Guest company website: https://www.bonfirevc.com/Host links:Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.They’ve scaled with us across funds and into the future.If your fund is growing in size or complexity, check them out at https://angellist.com/gtmfund.Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – Brett's career: Siebel, Salesforce employee #7, co-founder, angel investor, seed-stage VC06:58 – The big shift: from passive CRUD apps to agentic software that does the woThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Dan Wright (Co-founder & CEO of Armada) joins GTMnow to unpack what it actually takes to bring AI infrastructure to the places the cloud was never built to reach.The cloud covers about 30% of the world. The other 70% (think: oil rigs, the Arctic tundra, military ships, remote mines) is where some of the most critical decisions happen, making latency a life-or-death and billions of dollars difference. Armada is building the infrastructure for that part of the world: modular, ruggedized AI data centers that go to the data, instead of the other way around.From the first offshore edge computing deployment with the US Navy, to cutting avalanche response times in Alaska from over a day to real time, to sovereign AI installations in Saudi Arabia with Aramco and Microsoft, Armada is redefining what operating at the edge even means.In this episode, we cover:- Why cloud infrastructure was built for a pre-AI world and what that gap costs- How Starlink turned every remote location into a potential AI cluster- What "distributed intelligence" means and why it's the founding principle behind Armada- The global race for AI sovereignty and why modular compute is the linchpin- How Armada goes to market when a product demo involves shipping a 40-foot container to a desert (yes, really)- Why customer champions are better than any sales rep- The Microsoft partnership and how Armada extends Azure to places Azure could never go on its own- Category creation lessons from building a company before the market had a name for the industry- What's next: SpaceX, sovereign AI, and why Dan thinks humans are on the moon in two years (yes, REALLY)Guest links: Dan Wright - LinkedIn: https://www.linkedin.com/in/wrightdh/, hDan Wright - X: https://x.com/danwrightSFArmada - LinkedIn: https://www.linkedin.com/company/armadaai/Armada - Website: https://www.armada.ai/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X: https://x.com/sophiebuonaNewsletter: The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all.In this conversation, you’ll learn what brand actually means (hint: it's not your logo), how PLG companies make the leap to enterprise, why being obsessively close to your customers is a compounding advantage, and how AI is reshaping the marketing playbook without replacing the human craft that sets great brands apart.Guest links:- Guest - LinkedIn: https://www.linkedin.com/in/sheilavashee/ - Guest company - LinkedIn: https://www.linkedin.com/company/figma/- Guest company website: https://www.figma.com/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter: https://thegtmnewsletter.substack.comSponsors: - HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/- Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund  and get three months free with the code GTMFUND.Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – The brownie stand: why brand building started at age eight03:55 – How Sheila defines brand: it's what people say when you're not in the room05:08 – Joining Dropbox as the second marketing hire06:07 – Space Race: the campaign that defined Dropbox'The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Bill Binch (Operating Partner at Battery Ventures) joins GTMnow to share the operational frameworks he's built across 116 quarters on quota, and what actually changes when you move from driving revenue to advising an entire portfolio.Before Battery, Bill was employee #16 at Marketo, where he led sales from zero revenue through IPO and a Vista Equity acquisition. He then served as CRO at Pendo, helping scale ARR to nearly $100M in only three years. His career spans some of the most defining sales organizations in enterprise software, from Oracle to PeopleSoft.- Bill Binch - LinkedIn: https://www.linkedin.com/in/bill-binch-302a4a2/, - Battery Ventures - LinkedIn: https://www.linkedin.com/company/battery-ventures/- Battery Ventures website: https://www.battery.com/Host links:- Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/- Max - X: https://x.com/HackItMax- Paul - LinkedIn: https://www.linkedin.com/in/paulsirving/- Paul - X: https://x.com/PaulGTM- Newsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.They’ve scaled with us across funds and into the future.If your fund is growing in size or complexity, check them out at https://angellist.com/gtmfund.Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:0The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Dan Lee (Co-Founder & CEO of Nooks) joins GTMnow to give a behind the scenes on how Nooks is launching a new Agent Workspace and AI Sequencing layer designed to operate across the full action set of a rep’s day — calls, emails, research, prospecting, and strategy.The conversation explores why top of funnel is changing the fastest, why traditional sequencing tools optimize the “move” but not the strategy, and how AI systems that learn from rep behavior can compound advantage over time. As adoption deepens, automation can move from ~40% of outbound execution toward 70% and beyond, while switching away resets that intelligence.We also discuss the broader category shift: customers pushing AI-native tools to take on incumbents, the rise of agent workspaces as the new interface for GTM teams, and why calls remain the most data-rich channel in outbound compared to silent email non-responses.Guest links: Guest - LinkedIn: https://www.linkedin.com/in/dan9lee/Guest company - LinkedIn: https://www.linkedin.com/company/nooksapp/Guest company website: https://www.nooks.ai/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund and get three months free with the code GTMFUND.Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – Announcing the Agent Workspace and AIThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Emir Atli (Co-founder and CRO of HockeyStack) joins GTMnow to share how go-to-market is shifting in the AI era — from fragmented tools and GTM sprawl to unified, AI-native platforms built on a single data foundation.Originally known for attribution and market intelligence, HockeyStack is evolving into a central operating system for go-to-market, spanning marketing, sales, and post-sales through AI agents, blueprints, and an execution layer.We also explore weekly GTM sprints, founder-led content as a pipeline driver (even with <100 followers), and the long-game mindset behind building a generational company from age 20 after YC.In this episode, we cover:- Why you can’t layer AI onto legacy GTM — you must rebuild GTM around AI- The “sprawl crisis” and why siloed tools break without a single data foundation- HockeyStack’s evolution from attribution to a unified GTM operating system- AI agents, blueprints, and the shift from reporting to execution- Why consolidation is moving from tools to full buyer journey control- The case for a winner-takes-all GTM platform- How AI increases leverage across reps, managers, and pipeline reviews- Weekly GTM sprints and faster iteration cycles in the AI era- Founder-led content as a core growth engine and pipeline driver- LinkedIn as a top channel for MQL-to-opportunity and deal acceleration- The 10-year mindset, YC lessons, and building a generational companyGuest links: Emir Atli - LinkedIn: https://www.linkedin.com/in/emiratli/- HockeyStack - Website: https://www.hockeystack.com/- HockeyStack - LinkedIn: https://www.linkedin.com/company/hockeystack/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter: https://thegtmnewsletter.substack.comSponsors:Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/?via=gtmfund&dub_id=ytmcNnCjtlqCbgH5 and get three months free with the code GTMFUND.Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – The GTM sprawl crisis and why AI breaks in siloed systems01:50 – From attribution to a GTM operating system02:41 – Launching AI agents, blueprints, and the execution layer in 202603:57 – Building a single data foundation across the buyer journeyThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Amanda “Robby” Robson (Founder of Modern Technical Fund) joins GTMnow to break down how she evaluates companies at the very earliest stages and why discipline matters more than ever in today’s market.Amanda has spent over a decade in venture before launching Modern Technical Fund, investing across verticals ranging from security and compliance to developer tools at firms like Norwest and Cowboy Ventures. Her investment thesis is centered on backing elite technical founders early and helping them translate deep engineering talent into real products, real customers, and real momentum.In this conversation, we unpack how Amanda thinks about founder quality, market timing, and risk when there’s limited data and plenty of noise, which is more critical than ever in an AI-heavy investing environment.Guest LinksAmanda’s LinkedIn: https://www.linkedin.com/in/amanda-robson-7227685b/Amanda’s Twitter: https://x.com/robby_mtfModern Technical Fund’s LinkedIn: https://www.linkedin.com/company/modern-technical-fund/Modern Technical Fund website: https://moderntechnicalfund.com/Host links: Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.They’ve scaled with us across funds and into the future.If your fund is growing in size or complexity, check them out at The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved.Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based pricing model backed by up to a $1M performance guarantee if resolution targets aren’t met.In this episode, we cover:- Why customer support is fundamentally a 24/7 business- How Fin now handles 80%+ of customer queries through automation- Why human empathy often breaks down in real-world support workflows- How AI makes instant, individualized service possible for the first time- Why Intercom put a million-dollar guarantee behind its resolution rate- What it takes to confidently price software on outcomes- Why the future of support is humans + AIGuest links: - Archana Agrawal - LinkedIn: https://www.linkedin.com/in/archana-agrawal/- Intercom - LinkedIn: https://www.linkedin.com/company/intercom/- Intercom’s Fin Agent: https://fin.ai/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter: https://thegtmnewsletter.substack.comSponsors: HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/?utm_medium=podcast&utm_source=gtmfund&utm_campaign=intercom-episode  and get three months free with the code GTMFUND.Transcript available under the episode here: https:/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies.Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall.In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator.In this episode, we discuss:- Why understanding customer pain matters more than having a great idea- Why early selling should optimize for learning, not revenue- Why founders can’t outsource sales too early- How distribution becomes a competitive advantage at scale- What makes “unlikely entrepreneurs” outperform expectations- Why small, high-quality teams beat large organizations- Why churn is a symptom, not the root problem- How product-market fit quietly changes as companies grow- Why founders must evolve from heroic sellers to system builders- How culture becomes a real go-to-market assetLou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer.If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most.Timestamps:00:00 – What actually makes a company great00:26 – Why early selling is about learning, not revenue01:47 – Why founders misunderstand customer pain02:06 – “If you build it, they will come” is a lie02:33 – Distribution as the real moat02:58 – What makes an “unlikely entrepreneur” succeed06:15 – Why age and experience increase founder success07:01 – Curiosity, coachability, and risk elimination09:29 – Why founders can’t outsource sales too early15:26 – Pattern recognition vs short-term ARR21:10 – Founder-led sales vs scalable systems29:12 – Leadership, culture, and delegation33:18 – Founder evolution from $1M to $100M38:24 – When product-market fit starts to break39:15 – Why churn is a lagging indicator39:54 – Why small teams outperform large ones44:22 – Lessons from Unlikely Entrepreneurs45:23 – Final advice for foundersSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.comGuest links:LinkedIn: https://www.linkedin.com/in/loushipley/X: The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events.As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition.In this episode, we discuss:- Why in-person events are becoming a premium GTM channel in an AI-first world- How founders can de-risk distribution before building the product- The most common internal missteps that derail startups early- Why offsites are the new HQ for remote and hybrid teams- How to design offsites that drive alignment, not just fun- What makes a dinner actually work — including overlooked details like acoustics- How teams use events for customer acquisition and partnerships- Why kindness and positivity can be a real leadership advantageHealey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world.Timestamps:00:00 – Why founders underestimate distribution03:30 – Product vs distribution: what actually matters early06:45 – Why most startups fail from internal misalignment10:30 – Culture, communication, and focus as scaling constraints14:40 – Hybrid work broke alignment17:45 – Why offsites are becoming the new HQ21:30 – Events as a go-to-market strategy25:00 – AI, outbound fatigue, and inbox trust collapse28:40 – “In-person experiences are becoming a premium”32:30 – How to use events for customer and partner acquisition36:15 – What makes a high-impact event vs a wasted one39:50 – Dinners, summits, and unforgettable experiences43:30 – Leadership, kindness, and “don’t be a jerk”47:40 – Mental state as a competitive advantage52:30 – Final reflections and advice for foundersSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.comGuest links:Instagram: https://www.instagram.com/healeycypher/?hl=enHealey’s podcast: https://www.dontbeajerkpodcast.com/Mentioned Resources:Host (Sophie Buonassisi) links:X (Twitter): https://x.com/sophiebuonaNewsletter: The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Why do so many go-to-market motions fall apart right when a company starts to scale?In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.In this episode, we cover:Why most GTM motions fail at scale, even with strong productsWhat it really means to treat go-to-market like a productHow AI changes execution without changing fundamentalsThe rise of the forward deployed engineerWhy “lost on price” is usually a lieWhat great sales reps still do better than anyone in the AI eraHow to think about joining companies “early” without getting timing wrongListen if GTM feels fragile, unpredictable, or overly dependent on heroes.Timestamps00:00 – Introduction01:00 – “Yes is great. No is great. Maybe will kill you.”02:00 – Why go-to-market should be treated like a product04:45 – Designing the experience of being sold to06:30 – Using AI to debug GTM process failures09:00 – Why “lost on price” usually isn’t about price12:00 – What go-to-market engineering actually is16:00 – The rise of the forward deployed engineer20:45 – AI, agents, and what still needs human judgment25:45 – What great sales reps do differently in the AI era29:30 – Why GTM roles are becoming more consultative33:30 – Will there be an AI reckoning?38:00 – What “joining early” really means42:00 – Career lessons from Google, Stripe, and Vercel44:00 – Closing thoughts The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping the company navigate hypergrowth. Discussed in this episodeWhy Mark studied international relations, and why venture feels like “the liberal arts of jobs”Index’s US “invisibility” era and what that taught him about building a new firmThe Chemistry spinout thesis: “take great multi-stage DNA, reconstitute it with focus”Fund design: pre-seed → seed → A, light reserves, and concentrated doubling-downHiring strategy: network access > spreadsheet diligenceCulture principles: excellence, performance, “no one takes themselves too seriously”Conviction-based investing vs consensus IC, and why omissions are the real killerThe hardest lesson in venture: managing co-founder dynamics (and when to just listen)Episode highlights00:00 — “A+ people want to work with A+ people.”01:46 — GTMfund’s 2026 prediction: big players come roaring back (Google, Meta, Microsoft, Uber/Waymo).14:51 — GTMfund platform metrics: thousands of support items, intros, hires, and fundraising connects.26:29 — Why Mark left Index to build Chemistry: big-fund lessons, rebuilt with focus.33:39 — Chemistry’s strategy: early-stage focus, light reserves, and building for “product-market discovery.”44:05 — “Venture doesn’t scale well.” Why Chemistry stays small to avoid bureaucracy.49:59 — Events that actually work: chess tournaments, surfing, and hobby-driven gathering > happy hours.54:56 — Investment process: conviction, not consensus—optimize for outliers, not averages.1:10:32 — Hardest lesson in venture: co-founder dynamics, and learning when to listen (not “advise”).Brought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture. They’ve scaled with us across funds and into the future.If your fund is growing in size or complexity, check them out at www.angellist.com/gtmfund.Follow Mark GoldbergLinkedIn: https://www.linkedin.com/in/mark-goldberg-25458110X (Twitter): https://x.com/Mark_Goldberg_X (formerly Twitter)Chemistry (website): https://www.chemistry.vc/ChemistryThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100.Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Objects, and IBM. He is also a General Partner at GTM Operators Network, investing from seed through growth, and is deeply committed to mentorship and advancing underrepresented leaders in tech.Discussed in this episode:Why “AI-led growth” can hide churn and value erosionLagging vs leading indicators for retention enduranceWhy the CS investment benchmark is shifting from 10% → ~7%A simple “waterfall” for allocating post-sales budget: support → onboarding → outcomesHow to “lever up” the envelope with premium support + professional servicesWhy expansion (not renewals) is the early signal of product-market fitThe rise of AI-powered specialized generalists in post-salesWhen forward deployed engineers make sense (and when they’re just a fad)Episode highlights00:00 — Why customer expansion is the real signal of product-market fit00:50 — Lagging revenue vs. leading indicators of endurance04:11 — Why the CS benchmark dropped from 10% to 7%08:41 — How AI moved from internal efficiency to customer-facing leverage11:41 — Why retention cost matters more than CAC in the AI era14:17 — The simplest framework for allocating the 7% CS budget18:53 — Founder-led CS, design partners, and early-stage PMF myths23:16 — The rise of AI-powered specialized generalists30:00 — When forward-deployed engineers actually make sense49:31 — The one rule for building a durable SaaS companyThis episode is brought to you by our sponsor: HockeyStackIf you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next.HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale what works. That’s why teams like RingCentral, Outreach, ActiveCampaign, and Fortune 100 companies rely on HockeyStack to eliminate wasted spend, take better decisions, and make space to think.Learn more at hockeystack.comFollow Abbas Haider AliLinkedIn: https://www.linkedin.com/in/abbashaideraliX (Twitter): https://x.com/abbashaideraliGitHub: https://github.com/AbbasHaiderAliFollow Sophie Buonassisi (Host)LinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.com The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Adam Carr is the Chief Revenue Officer at Apollo, where he’s scaling revenue by layering sales on top of a $150M+ ARR product-led growth engine. Previously, Adam helped scale Miro from a PLG-led company into a global sales organization, contributing to its growth into a $17.5B business. He’s known for building systems-driven GTM teams that turn product signals into durable revenue.Discussed in this episodeWhy PLG is gravity (signals + acquisition) and sales is the monetization layerThe “one-team” model to prevent PLG vs. sales cannibalizationBuilding talent density (and why slowing hiring can be the fastest path)Hiring for curiosity, coachability, ownership, and team-first executionThe “architect / systems thinker” profile for modern sellersA new post-sales model: CSMs → technical GTM Engineers + intervention-led journeyUsing customer journey milestones to drive expansion and prevent churn proactivelyAI in GTM: streamlining manual work so humans focus on better conversationsEpisode highlights00:00 — PLG is about signaling + acquisition (not monetization)01:30 — “PLG isn’t the monetization way… it’s layering sales.”02:41 — Talent density: hire for the next 12–18 months, not just “today”04:50 — The soft skills that scaled Miro: curiosity, coachability, ownership08:38 — Why Adam hires “architects” (system thinkers) instead of just sellers10:41 — The mindset shift: celebrate value realized, not contracts signed15:41 — Replacing CSMs with “go-to-market engineers” + an intervention model19:14 — Turning PLG signals into PQA/PQL routing (and reducing the “noise”)29:26 — “100M ARR is late” — when to start layering sales into PLGGuest linksLinkedIn (Adam Carr):https://www.linkedin.com/in/adamhcarrFollow Sophie Buonassisi (Host)LinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comWhere to Find GTMnowWebsite: https://gtmnow.comLinkedIn: https://www.linkedin.com/company/gtmnowX (Twitter): https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowPodcast Directory: https://gtmnow.com/tag/podcastThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board.Discussed in this episode:How Cassie “accidentally” became a VC after 15 years in GTM leadership.The career advice Bill Gurley gave her that changed her trajectory.Why Primary refuses to say “platform” and instead built a 30-person Impact team.How she actually sources pre-seed/seed founders before they leave their jobs.Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).The difference between real traction vs. “happy ears” and fake design partners.Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.How operators can actually break into VC (hint: it’s all about doing the work).Episode highlights00:35 — Clay, usage-based pricing, and the $100M ARR rocketship09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t)14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”)46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features1:01:29 — So you want to be a VC: Cassie’s playbook for operators to break into venture (without delusion)Brought to you by: AngelListHow did we build the GTMfund back office? Easy!We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.Discussed in this episodeWhy classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.How the Bowtie model exposes the real levers of growth that funnels hide.Why PLG-style thinking is now essential even for sales-led and enterprise motions.The 3 first principles of freemium: empathy, generosity, and metrics.Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.How to design hybrid human + AI workflows using a clear data model, not vibes.What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.Episode highlights00:00 — GTM is still running 20-year-old playbooks01:29 — “Sales, marketing, CS… the last unengineered engine”03:20 — The myth of “just add more heads”05:50 — The Fundly story: reinvention, too late08:30 — Why Freemium had to be written11:01 — Three first principles of freemium15:25 — Mapping AI across the entire customer journey19:29 — “Automate the predictable, humanize the exceptional”25:18 — What the Bowtie exposes that funnels hide27:25 — Building a “minimum viable BowtieThis episode is brought to you by our sponsor: ZoomInfoZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Dave Boyce (Guest)LinkedIn: https://www.linkedin.com/in/boycedaveSubstack: https://daveboyce.substack.comWhere to Find GTMnowWebsite: https://gtmnow.comLinkedIn: https://www.linkedin.com/company/gtmnowX (Twitter): https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowPodcast Directory: https://gtmnow.com/tag/podcastThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.Discussed in this episodeThe evolution of partner selling — from VARs to SIs to ecosystemsHow to know if partner selling fits your GTM modelThe delivery-first mindset that drives retentionDirect vs. partner motion: Microsoft vs. SalesforceWhy enablement is the #1 green flag for partner successPartner marketing: how to make resellers self-sustainingUsing AI to power future-ready GTM modelsThe case for hybrid work in high-performance sales culturesEpisode Highlights00:00 — The “year four” moment when partners are selling for you01:07 — 30 years of selling through partners in New York03:22 — Start partner strategy with delivery, not distribution06:32 — Why partner selling creates “superhuman” sellers09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid12:13 — The startup hack: sell delivery on your paper, subcontract partners17:16 — A 90-day playbook for integration partnerships21:39 — Hiring the right people to build a partner business27:18 — How Sisense runs delivery partners and an Australian reseller29:55 — White-labeling Snowflake: using resell to get the giant’s attentionThis episode is brought to you by our sponsor: BoomPopWe’re deep in event planning right now, as no doubt many of you are.Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.Follow Brian WeinbergerLinkedIn:https://www.linkedin.com/in/brianweinbergerRecommended BooksWhat Great Salespeople Do by Michael Bosworth & Ben Zoldan — The power of storytelling in salesThe Power of Nice by Linda Kaplan Thaler & Robin Koval — Why kindness compounds in businessSacred Hoops by Phil Jackson — Coaching and leadership lessons from the Bulls dynastyReferencedSisense: https://www.sisense.comSnowflake: https://www.snowflake.comAWS: https://aws.amazon.comSalesforce: https://www.salesforce.comMicrosoft: https://www.microsoft.comAccenture (SI example): https://www.accenture.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.This is a clip from the full episode with Cristina (an inside look at the judgment frameworks behind Stripe, Notion, and now Linear) and the practical filters every GTM leader can use to pick winners early.Discussed in This ClipHow to recognize “exceptional” even outside your own domainFinding early proof a product is truly beloved (signals > vanity metrics)Starting with a sharp market wedge, then earning the right to expandWhy founders who excel at something—anything—tend to excel at company-buildingWhat to expect from early operators: founder mode and bias to executeSales hiring for technical buyers (and why quotas can help earlier than you think)Aligning tightly with founders as an exec: relationships drive outcomesHow to assess GTM on day one: ride-alongs, raw customer feedback, ground truthHighlights00:00 — The difference between good and great—and how to spot it across functions00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)12:52 — What great early leaders do: see problems, create strategy, then execute16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observationThis episode is brought to you by our sponsor: BoomPopWe’re deep in event planning right now, as no doubt many of you are.Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Alex Clayton is one of the clearest minds in growth-stage investing, the person elite founders turn to when the market is noisy and the stakes are high. A General Partner at Meritech Capital, Alex has built a reputation for breaking down complex businesses with uncommon clarity, from his legendary S-1 teardowns to his frameworks on power laws, secondaries, and AI-native growth. Before Meritech, he honed his craft at Spark Capital and Redpoint, backing breakout companies like Braze, JFrog, Outreach, Pendo, Duo Security, and RelateIQ. A former ATP tennis pro and Stanford team captain, Alex brings that same discipline, pattern recognition, and competitive fire to evaluating the next generational companies.Discussed in this episodeWhy GAAP revenue and cash burn are the two metrics that quietly govern everything.How AI is changing growth rates, margins, and what “good” looks like in SaaS.The rise of secondaries, and why they now rival or exceed IPO volume.How to read an S-1 like a pro (and what Alex looks for first).Founder ownership, fund lifecycles, and how long companies really stay private.Why power laws in venture are getting even steeper in the AI era.How AI is reshaping pricing models from seats to usage and outcomes.Which iconic private companies are most likely to go public in the next 3 years.Episode highlights02:40 — Is the IPO window really back? 05:10 — Secondaries quietly outpacing IPOs08:10 — The only two metrics that matter10:56 — AI growth that breaks SaaS mental models26:20 — From “software” to “SaaS” to “AI”… and back again29:25 — Seat-based pricing vs outcome-based AI pricing34:55 — The capital tidal wave & longer private lives44:00 — Bubble vs biggest opportunity of our careers57:17 — What the rest of the 2020s look like1:03:41 — Why GAAP revenue + cash burn still winBrought to you by: AngelListHow did we build the GTMfund back office? Easy!We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.Follow Alex ClaytonLinkedIn: https://www.linkedin.com/in/aclaytonX (Twitter): https://x.com/afcFollow Max Altschuler (Host)LinkedIn: https://www.linkedin.com/in/maxaltschuler/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Chris Degnan is the former Chief Revenue Officer of Snowflake, where he helped scale the company from pre-product to over $4B in ARR and more than $100B in market cap. Over his 11-year tenure, Chris built Snowflake’s go-to-market engine from the ground up, from personally running the first outbound campaigns to leading a global sales organization through four CEOs and one of the largest software IPOs in history.Today, he advises founders and revenue leaders on how to build high-velocity GTM teams, hire with grit, and scale with discipline. Chris is also the co-author of Make It Snow, the definitive playbook on Snowflake’s go-to-market journey, co-written with CMO Denise Persson.Discussed in this episodeThe early days of Snowflake: selling a stealth startup with no productHow to hire and identify truly self-motivated, gritty sales talentThe lessons from John McMahon that shaped Snowflake’s leadership DNAHow to build sales-marketing alignment that actually scalesThe near-death experiences that almost killed SnowflakeWhat great CEOs do differently, from Muglia to SlootmanThe power of focusing on new logo acquisitionThe evolution of sales methodologies: MEDDPICC, culture, and curiosityThe truth about AI’s “bubble”, and what’s real beneath the hypeEpisode highlights00:02:21 — Why join Snowflake pre-product and in stealth.00:05:36 — The original outreach script and what resonated with prospects.00:06:49 — Scaling from lists to SDRs; Degnan’s “8 meetings per week” rule.00:09:11 — Hiring for self-starters; the interview opener: “Tell me your life story.”00:12:49 — The feedback loop that kept a CRO in seat for 11 years.00:24:46 — The outage that almost killed Snowflake, and how leadership showed up.00:28:34 — New logo gates every quarter and why it mattered more than anything.00:34:05 — “Customer success is everyone’s job”: removing CS, monetizing PS, driving adoption.00:36:40 — Databricks: where Snowflake ceded ground and what they’d do differently.00:39:19 — Why going public was the right move for enterprise trust.This episode is brought to you by our sponsor: BoomPopWe’re deep in event planning right now, as no doubt many of you are.Whether it’s an offsite, conference, or any other kind of event,BoomPop makes that happen with end-to-end planning all in one place.They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.Follow Chris DegnanLinkedIn:https://www.linkedin.com/in/chris-degnan-524470Make It Snow (book):https://makeitsnowbook.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Michel Tricot is the co-founder and CEO of Airbyte, the open-source data movement platform he launched in 2020. Before Airbyte, Michel led integrations and served as Director of Engineering at LiveRamp, where he scaled the teams and pipelines that synced massive data volumes. He also helped build rideOS as a founding engineer and Director of Engineering. Michel has spent 15+ years in data infrastructure, with a focus on commoditizing data pipelines and giving teams control and sovereignty over their data. Discussed in this episodeWhy Airbyte launched open source first (catching engineers “at the search”)Project-market fit vs. product-market fit, and why they’re differentThe content engine: founder-led writing, shipping slides, and radical transparencyTurning interest into community: 25k+ Slack, champions, and hiring from withinThe near-misses: hiring ahead of PMF, support-heavy community, cloud complexityGoing upmarket: enterprise motion, longer cycles, and team ramp realitiesAI wave → agents as “data consumers” and what it means for pipelinesReplatforming for control & sovereignty, not just “more connectors”This episode is brought to you by our sponsor: ZoomInfoZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Michel TricotLinkedIn:https://www.linkedin.com/in/micheltricotX (Twitter):https://x.com/MichelTricotWebsite:https://airbyte.com/AirbyteHost linksLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.com/Website: https://gtmnow.com/Where to Find GTMnowWebsite: https://gtmnow.comLinkedIn: https://www.linkedin.com/company/gtmnowX (Twitter): https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowPodcast Directory: https://gtmnow.com/tag/podcastThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Tessa Whittaker is the VP of Revenue Operations at ZoomInfo, where she leads a 70-person global team powering one of SaaS’s most efficient $1B+ revenue engines. Over the past decade, she’s helped architect the systems, cadence, and AI workflows that underpin how ZoomInfo operates at scale.Tessa is known as one of the most thoughtful operators in tech, bringing structure, clarity, and rigor to how GTM organizations run. Her work sits at the intersection of data, process, and execution, proving that with the right operating cadence, even the most complex go-to-market systems can move in rhythm.Discussed in this episodeBuilding a personal operating system (Salesforce's V2MOM, Notion, weekly reviews) that maps vision → methods → measurable actions.“Operating rhythm” for GTM: the meetings, reviews, and enablement that create predictable execution.Color-coding calendars to align time with quarterly KPIs (and fixing misallocation).Counterintuitive up-market move: automate down-market so scarce humans focus on enterprise.AI intake & prioritization agent: compressing 10–15 hrs of RevOps scoping into one interaction.Democratizing creation: org-wide agent “hackathons,” usage leaderboards, and adoption lessons.Health OS during sprints: cut alcohol, protect sleep, simplify to sustain output.What to buy vs. build; auditing tech stacks; avoiding (and accepting some) agent sprawl.Episode highlights00:00 — Systems beat motivation; why cadence creates consistency.01:36 — RevOps as connective tissue of SaaS; the “invest earlier” regret.03:58 — From EA to SVP-level ops leader to VP RevOps: the long workback.06:51 — Why operators obsess over simplifying complexity.12:24 — Time as the scarcest resource: color-coding calendars to goals.20:05 — The RevOps operating rhythm at ZoomInfo (and how AI slots in).21:48 — Going upmarket? Automate downmarket first to free resources.31:19 — Intake agent: collapsing 10–15 hours of back-and-forth into one interaction.36:48 — Democratizing creation: internal agent hackathons and a usage leaderboard.44:30 — The Alchemist and reframing growth: get uncomfortable to keep climbing.This episode is brought to you by our sponsorsThe best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.If you’re hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.Guest links LinkedIn: https://www.linkedin.com/in/tessa-whittaker-44903940Where to Find GTMnowWebsite: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/X (Twitter):https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowThe GTM Podcast: https://gtmnow.com/tag/podcast/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Peter Grant is the Chief Revenue Officer at You.com, the AI search and productivity platform reshaping how people find and create information. A veteran GTM leader, Peter has built and scaled revenue engines at some of tech’s most iconic companies — from Siebel Systems to Salesforce to C3.ai — working directly under legends like Tom Siebel and Marc Benioff. Today, he’s leading You.com’s charge against giants like OpenAI and Google, bringing precision, storytelling, and speed to the most transformative era in technology.Discussed in this episodeHow Peter defines “the biggest opportunity of our lifetime” in AILessons from working under Tom Siebel, Marc Benioff, and Rishi KhoslaHow to hire SEAL-Team-Six-level GTM talentWhy belief and speed are non-negotiables when competing with giantsYou.com’s differentiation strategy against OpenAI and GoogleHow to operationalize AI literacy and agentic workflowsThe ROI gap in generative AI adoption, and how to fix itBuilding products that stand on truthEpisode Highlights00:14 — The biggest opportunity in technology this century05:25 — Lessons from working directly with Thomas Siebel06:41 — How to hire “SEAL Team Six” sales talent10:24 — Why “train hard, fight easy” defines great enablement20:08 — The new sophistication bar for AI literacy in sales25:14 — How You.com differentiates against OpenAI & Google30:00 — Peter’s personal AI productivity system: 40 agents40:12 — Speed, truth, and trust: You.com’s go-to-market culture48:30 — The “war room” story: building a sales plan overnight59:45 — No easy days: why startup life mirrors special forcesThis episode is brought to you by our sponsor: BoomPopA quick pause to spotlight a partner that helps GTM teams actually connect—BoomPop.Your next big unlock might not come from another meeting… it’s from getting your team in the same room. BoomPop makes that happen with end-to-end offsite planning all in one place.They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.And as a listener of GTMfund, you’re eligible for full-service event planning for just $99 per person (terms apply).Head to boompop.com/gtmfund to start planning your offsite.Guest LinksLinkedIn: linkedin.com/in/peterkgrantCompany: you.comRecommended BooksThe Hard Thing About Hard Things by Ben HorowitzElephants Can’t Dance by Louis V. Gerstner Jr.The Master Algorithm by Pedro DomingosNo Easy Day by Mark Owen — a favorite for its lessons on grit and resilienceThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

This bonus episode dives into how Rick Kelley helped scale Meta’s global sales organization (from 900 employees to 90,000) and the playbook behind building high-performing international teams.Rick Kelley is the former SVP of Gaming and App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization and played a pivotal role in building out Meta’s go-to-market teams across North America and EMEA. Over his 15-year career at Meta, Rick was instrumental in driving international expansion, especially across Europe, the Middle East, and Africa—helping to localize strategy, scale high-performing sales teams, and bring new ad products to market. Today, he advises founders on global GTM execution, sales hiring, and how AI is reshaping the future of commercial organizations.This is a clip from the full episode with Rick, an inside look at how Meta built its $1B EMEA business and the lessons every GTM leader can apply to scale globally.Discussed in This Clip:The exact framework Rick used to decide which EMEA markets to enter firstHow Meta built a $1B+ regional business from just three salespeopleThe power of centralization in early-stage go-to-marketWhy you should plan every headcount allocation before hiringCreating “optionality” in your sales org to weather changeHow gaming became Meta’s fifth global regionWhen to localize sales teams versus staying centralizedWhy AI can make sales more efficient—but can’t replace relationshipsHighlights00:12 — Scaling Meta: from 900 to 90,000 employees01:22 — How Rick Kelley built Meta’s mid-market sales org from scratch02:15 — The data-driven framework Meta used to prioritize global markets04:50 — Why startups should build expansion plans before executing07:52 — Centralized vs. in-country hiring: Rick’s take for startups09:49 — The importance of sales ops and forecasting discipline13:32 — Hiring leaders who scale with you, not limit you14:59 — How AI will reshape (but not replace) sales relationships16:09 — From zero to $1B: lessons in efficiency, cost, and cultureThis Episode Is Brought to You ByZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps. By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Rick KelleyLinkedIn:https://www.linkedin.com/in/rickkelley/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.Discussed in this episodeWhy AEO is an evolution of SEO (and what truly changes)The shift from keywords to “clusters of questions” as the new topic modelWebflow’s four-part AEO framework: content, technical, authority, measurementTactics that moved the needle: adding FAQs + schema; prioritizing freshnessWhy PR/brand and plain-text mentions matter more to AI enginesHow to measure AEO: presence in questions, share of voice, and sentimentWhere to start: two moves any founder can ship this weekRisks of ignoring AEO and the early-adopter advantageEpisode highlights00:21 — “Your SEO resources are your AEO resources. This is an evolution, not a reset.”01:15 — Webflow’s AEO promise: answer engines are a massive arbitrage—akin to early SEO/SEM/mobile.03:00 — Why “ranking for keywords” is obsolete; topics = clusters of questions across the funnel.07:49 — The 4-part AEO framework: content, technical (schema & structure), authority, measurement.10:11 — Case study: Add ~6 FAQs + inline schema to product pages → half of new citations came from 6 pages; +24% organic in 2 weeks.15:23 — If you only do two things: (1) answer questions comprehensively, (2) add schema metadata.21:46 — Webflow data: AI-search traffic converts ~6x better than non-branded organic; unbranded share grew from 0% → 42% in a year.24:02 — How buyers actually use LLMs in-flow; why your website still matters (to humans and machines).29:58 — The learning curve is back: why AEO is resetting the playing field and rewarding curiosity.This episode is brought to you by our sponsor:ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth.With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Guy Yalif:LinkedIn: https://www.linkedin.com/in/gyalif/X (Twitter): https://x.com/gyalifX (formerly Twitter)Webflow author page: https://webflow.com/people/guy-yalifThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, he’s at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will define the next era of software companies.Discussed in this episodeWhy prompting and context engineering are the most important skills for GTM operatorsHow “vibe prompting” accelerates learning and output with LLMsThe three keys to building AI fluency inside teamsMeasuring ROI from AI across sales, marketing, and operationsWhy every professional is now a manager (of AI agents)How websites will evolve into multimodal closing mechanismsThe rise of personality-led growth in B2B marketingWhy curiosity and persistence matter more than ever in an AI-first worldEpisode highlights00:46 — The 100x difference between good and bad prompting03:57 — The rise of “context engineering” as a GTM skill07:22 — Kieran’s 3-part framework for AI fluency inside teams09:31 — Why “vibe prompting” is as powerful as vibe coding11:00 — How AI boosts conversions & deal velocity in sales workflows15:10 — Using ChatGPT memory as a personalized prompting coach22:19 — Everyone now manages a PhD-level AI intern31:12 — The 3 biggest shifts coming to GTM: influence, AI optimization, multimodal37:42 — Why AI makes human creativity more valuable than ever43:06 — The grind, reps, and curiosity as the ultimate AI skillsBrought to you by: MutinyAre you a B2B Marketer running campaigns for target accounts? Then you know the struggle: tedious and manual processes, endless delays to get things live, and sales feeling like you’re not doing enough.That’s where Mutiny comes in. Mutiny is the fastest place to launch breakthrough campaigns for your target accounts. AI agents research your accounts, build personalized landing pages, and scale everything from LinkedIn ads to sales handoffs, all in one seamless workflow. No more stitching tools together. Just smarter, more impactful campaigns powered by real data. Launch in days, not weeks.See why teams who use Mutiny generate 3X more account engagement.Book a demo at mutinyhq.comGuest linksLinkedIn: https://www.linkedin.com/in/kieranjflanagan/Newsletter (The AI Marketing Generalist):https://www.kieranflanagan.io/Podcast (Marketing Against the Grain):https://www.youtube.com/@MATGpod/videosHost linksLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X (Twitter): https://x.com/sophiebuona Newsletter: https://thegtmnewsletter.substack.com/ Website: https://gtmnow.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.Discussed in this episodeWhy Cristina joined Stripe without knowing what an API wasBuilding Stripe’s early partnerships and salvaging the Shopify dealHow Notion pioneered community-driven growthLessons on brand, design, and investing for the long termWhat Cristina looks for in exceptional founders and operatorsHow Linear is scaling GTM with AI-driven prioritizationThe difference between “keeping the lights on” and transformative leadershipCristina’s frameworks for evaluating product resonance and customer loveEpisode Highlights00:43 — The rare superpower behind Cristina’s career: joining breakout companies early2:46 — Why Cristina joined Stripe without knowing what an API was12:22 — On Cristina’s first day, Shopify walked away from Stripe’s deal — and how she won them back16:55 — How Notion scaled by making consumer use free and fueling community-driven growth20:52 — Why investing in brand early is a leading indicator of durable growth25:27 — Cristina’s framework for spotting beloved products in the market37:53 — How Cristina applied lessons from Stripe to build Linear’s GTM from scratch47:30 — Where AI fits into GTM: prioritizing opportunities, not replacing humans56:01 — Why Linear built high-quality swag kits for early customers58:28 — Where to follow Cristina’s journey todayThis episode is brought to you by our sponsorHarmonic helps you discover the best startups way ahead of the competition. We use it at GTMfund, as do thousands of investors at firms like USV and Insight. GTM teams at companies like Notion and Brex also rely on the platform to stay ahead.Harmonic tracks millions of startups and lets you search using simple filters or natural language to match exactly what you’re looking for. When you find a company that looks interesting, Harmonic pulls everything into one place (founder backgrounds, traction, and market data) so you can quickly evaluate and understand if it’s a fit.At GTMfund, we even have a private Slack channel called #companywatchlist powered entirely by Harmonic.Get 2 dedicated sessions with their team to help you test and structure the perfect searches here.Guest LinksLinkedIn: https://www.linkedin.com/in/cristinajcordovaX (Twitter): https://x.com/cjCThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Kyle Norton is the Chief Revenue Officer at Owner, the fast-scaling restaurant SaaS platform valued at over $1B. Since joining from Shopify, Kyle has helped grow the company from $2M to $50M+ in ARR by instilling a high bar for sales talent, building RevOps early, and driving a disciplined go-to-market strategy. A podcast host himself, Kyle shares deep expertise on sales hiring, leadership, and GTM AI, while keeping his focus on building a generational company.Discussed in This EpisodeWhy Kyle let go of half the sales team just 45 days inThe importance of setting a high bar for sales talent and cultural fitInvesting in RevOps and data foundations far earlier than conventional wisdomHow to reduce churn by narrowing ICP and saying no to misfit customersLessons from running hiring retros to assess interview process effectivenessThe balance between remote vs. in-office roles for scaling GTM teamsHow Owner approaches AI in go-to-market, starting with data over “shiny tools”Kyle’s leadership philosophy: servant leadership and building for growthEpisode Highlights00:44 — Owner’s journey from $2M ARR to unicorn02:01 — Kyle explains why he fired half the sales team just weeks into the role04:56 — Why Owner set a sky-high bar for early sales hiring08:13 — Kyle’s case for bringing in RevOps “too early” and why it paid off12:39 — Reducing churn by saying no to 30% of potential customers15:57 — Why hiring fit matters more than a candidate’s “pedigree”21:49 — What Kyle learned from running hiring retros on interview data30:25 — Owner’s AI GTM transformation: starting with third-party data48:34 — Kyle’s take on the remote vs. in-office debate for sales teams54:53 — His leadership philosophy: servant leadership + relentless coaching59:19 — Kyle’s essential reading list for sales leadersThis episode is brought to you by our sponsors:QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.PursuitThe best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.If you’re hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.Guest LinksLinkedIn:https://www.linkedin.com/in/kylecnorton/Podcast: https://therevenueleadershippodcast.com/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Ghazi Masood is the Chief Revenue Officer at Retool, where he leads the go-to-market engine for the low-code developer platform. Previously he served as SVP & GM, Americas at Auth0 after leadership roles at Microsoft, Oracle, Polycom, and Nintex K2, and he advises several high-growth startups on GTM. A field-first operator, Ghazi specializes in layering sales onto product-led motions and building enterprise upgrade paths without breaking self-serve growth.Discussed in this episodeThe moment inbound stops being enough—and how to size the outbound gapWhy to bifurcate SDRs (inbound vs. outbound) and how to define lead sourcesProfiling inbound (more technical, SE-adjacent) vs. outbound (AE-track) talentStructuring self-serve as a permanent home vs. a stepping stone to enterprise“Ungate to upgrade”: using sustained overage/feature use as a right-sizing triggerPricing & packaging that pulls larger accounts to annual, committed plansThe “GTM engineer” model for AI-native, high-velocity companiesHiring pace, capacity planning, and the leadership principles that scaleEpisode highlights00:00 — Inbound eventually caps out; annual planning exposes the pipeline gap that outbound must fill.00:45 — What it really takes to add sales to a product-led motion—without breaking PLG.03:23 — First move: bifurcate SDR into dedicated inbound and outbound to drive focus and outcomes.04:18 — Nail definitions with Marketing: what counts as inbound vs. outbound (e.g., events ≠ inbound).06:37 — Decide the role of self-serve: permanent home for some segments vs. stepping stone to enterprise.09:41 — Ungated features as signals: after ~3 months of sustained overage/premium use, “right-size” the plan.12:09 — Why frictionless adoption beats hard gates—and how clear web docs make the convo non-adversarial.15:10 — When to move from pay-as-you-go to annual: sophistication and committed usage, not arbitrary timing.18:51 — Enter the “GTM engineer”: one person spans SDR → SE → AE → AM to capture massive inbound demand.25:36 — Frameworks that still work: MEDD(P)ICC and Solution Selling 2.0 for complex, multi-product deals.Sponsor – PursuitThe best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.If you’re hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.Guest linksLinkedIn: https://www.linkedin.com/in/ghazi-masood-09195a2Company: https://retool.comHost linksLinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Paul Williamson is a seasoned go-to-market leader and advisor best known for helping Plaid scale from $3M to $300M ARR. As Head of Revenue, he built and evolved Plaid’s go-to-market roadmap across product-market fit, upmarket expansion, and new verticals. With deep experience aligning GTM with product, he now advises founders on sequencing bets, building forward-compatible roadmaps, and scaling revenue organizations with intention.Discussed in this EpisodeWhy GTM roadmaps should be “forward-compatible”Iteration cycles in GTM vs. product roadmapsEarly lessons from Plaid’s rudimentary qualification processRecognizing high-value clients vs. anti-patterns in inbound leadsHow daily standups created fast GTM learning loopsShifting from PLG to sales-led motions with SDRs and routingSequencing GTM expansion: fintech → enterprise FSIs → embedded fintechCompensation design mistakes and their impact on sales behaviorEpisode Highlights00:00 — Why GTM roadmaps should be built “forward-compatible”01:53 — How Plaid iterated through 9–10 GTM versions in the first year05:12 — Plaid’s early qualification process: 4 simple questions07:28 — Why most inbound leads weren’t equal—and how Plaid spotted patterns10:01 — Using daily standups twice a day to refine GTM qualification14:32 — How Plaid’s GTM roadmap evolved from monthly to yearly cycles20:46 — Moving beyond partnerships to diversify top-of-funnel channels24:53 — Scaling into enterprise financial institutions with tailored product needs27:09 — Entering phase three: embedded fintech with customers like Tesla30:00 — Compensation design mistakes that slowed deals and created riskThis episode is brought to you by: HarmonicHarmonic helps you discover the best startups way ahead of the competition. We use it at GTMfund, as do thousands of investors at firms like USV and Insight. GTM teams at companies like Notion and Brex also rely on the platform to stay ahead.Harmonic tracks millions of startups and lets you search using simple filters or natural language to match exactly what you’re looking for. When you find a company that looks interesting, Harmonic pulls everything into one place (founder backgrounds, traction, and market data) so you can quickly evaluate and understand if it’s a fit.At GTMfund, we even have a private Slack channel called #companywatchlist powered entirely by Harmonic.Guest LinksLinkedIn:https://www.linkedin.com/in/paulrwilliamsonHost LinksLinkedIn:https://www.linkedin.com/in/sophiebuonassisiX (Twitter):https://x.com/sophiebuonaNewsletter:https://thegtmnewsletter.substack.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Jenny He is the Founder and General Partner at Position Ventures, an early-stage venture fund that backs startups with strategic communications from day one. Previously, Jenny led comms at Square and has since helped hundreds of founders land coverage in top outlets like TechCrunch and Forbes. With deep expertise in positioning, storytelling, and PR, she’s on a mission to help startups craft differentiated narratives that drive credibility, legitimacy, and growth.Discussed in This EpisodeWhat PR actually is (and isn’t) for startupsThe difference between positioning, storytelling, and PR — and how they stack togetherWhen PR makes sense and when to hold back on announcementsStep-by-step process for landing coverage in top outlets like TechCrunch or ForbesHow to build authentic relationships with reporters before you pitchWhat makes something truly newsworthy: timeliness, impact, relevanceTactical advice for pitching, interviews, and amplifying coverage post-launchHow PR fits into the broader go-to-market motionEpisode Highlights00:00 — Positioning, storytelling, and PR defined02:23 — Jenny explains what PR really is and why startups misunderstand it06:39 — The first step before any PR push: setting clear goals11:37 — Example of a newsworthy founder story: building an AI radiologist from personal experience15:17 — The three elements of newsworthiness: timeliness, impact, and relevance17:42 — Why building warm relationships with reporters is crucial20:36 — Preparing for the interview itself vs. outreach22:47 — Amplifying coverage through your network post-publication25:07 — What PR agencies cost (and why no one can guarantee coverage)29:18 — Jenny’s #1 book recommendation on positioningThanks to Our Sponsor – Clarify:Clarify is the autonomous CRM built for founders and early-stage teams who want to build more pipeline, close more deals, and spend way less time on busywork.Clarify automatically enriches your contacts, captures leads from anywhere (even one click from LinkedIn), and keeps your pipeline up to date on its own, so you can focus on winning deals, not updating fields.If you’re looking to simplify your stack and help your team move faster, check out Clarify.Recommended BooksPositioning: The Battle for Your Mind by Al Ries & Jack Trout — Jenny’s #1 recommendation for founders learning positioning fundamentals.ReferencedClarify (autonomous CRM): https://clarify.aiTechCrunch: https://techcrunch.comForbes: https://forbes.com New Lantern (portfolio company example): https://newlantern.aiSquare: https://squareup.comGuest LinksLinkedIn: https://www.linkedin.com/in/jennyheX (Twitter): https://x.com/jennydhe Website: https://positionventures.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

James Roth is the Chief Revenue Officer at ZoomInfo, where he oversees a global revenue engine supporting over 37,000 customers and more than $1 billion in ARR. With a background in scaling hypergrowth teams and building enterprise go-to-market machines, James has helped reposition ZoomInfo from a sales tool to the foundational data layer for modern GTM teams. Under his leadership, ZoomInfo launched Copilot, its flagship AI product, and executed a bold shift upmarket — transitioning from transactional selling to a data-first, enterprise-driven GTM strategy.Discussed in This EpisodeHow ZoomInfo transitioned from transactional selling to enterprise go-to-marketThe "Good Co, Bad Co" framework for segment-specific product retentionWhy ZoomInfo changed its ticker symbol to GTMLaunching Copilot and driving $100M revenue in under 6 monthsHow internal AI usage became the go-to-market motionKey shifts in comp design and team segmentation for scaling upmarketUsing telemetry and real-time signal tracking to measure rep effectivenessLessons in long-term execution vs. short-term growth pressureEpisode Highlights00:00 — ZoomInfo's evolution from a sales tool to a data-first platform17:06 — Why data as a service is ZoomInfo’s fastest-growing business20:43 — How to build and apply the “Good Co, Bad Co” segmentation framework26:26 — The hard part about going upmarket? Aligning the full funnel org30:19 — Changing your ticker to GTM: A bold positioning play34:31 — Copilot’s $100M launch: The power of internal usage39:53 — Most AI tools show <5% revenue lift. Here's why43:29 — How ZoomInfo is operationalizing AI across the org48:29 — The signals > activity shift in modern sales measurement52:18 — What James wants future CROs to steal: Think long-term, build patientlyThanks to Our Sponsor – UserEvidence:UserEvidence is the Customer Evidence Platform that helps you collect feedback, surface proof points, and turn customer wins into bite-sized assets your sales and marketing teams can actually use. Capture social proof at scale. Arm reps with credible stories. Close more deals with trust.Learn more at: https://userevidence.com/gtmnowGuest Links LinkedIn: https://www.linkedin.com/in/james-roth-3a913b51/Host Links LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.com/Website: https://gtmnow.comWhere to Find GTMnow• Website: https://gtmnow.com• LinkedIn: https://www.linkedin.com/company/gtmnow/• X (Twitter): https://x.com/GTMnow_• YouTube: https://www.youtube.com/@GTM_now• The GTM Podcast: https://gtmnow.com/tag/podcast/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Stevie Case is the Chief Revenue Officer at Vanta, the $4B leader in trust management and compliance automation. Since joining in 2021, Stevie has scaled the company from sub-$20M ARR to north of $100M, navigated 40+ copycat competitors, rebuilt both pre- and post-sales engines, and led Vanta’s expansion from SMB into enterprise. A former world’s first female pro gamer turned tech sales leader, Stevie previously held senior roles at Twilio, where she helped grow the enterprise business to a $1B run rate. Discussed in This EpisodeHow Stevie’s path from pro gamer to CRO shaped her competitive edgeEarly-stage chaos at Vanta and the signs of undeniable product-market fitBattling over 40 copycat competitors with value selling and a “CIA” competitive squadWhy execution, not first-mover advantage, is the only sustainable moatThe challenges and lessons from scaling SMB sales and moving into enterpriseBuilding go-to-market experiments before committing product investmentTransforming post-sales into a growth engine and driving net retention upStevie’s view on AI in revenue operations and personal productivityEpisode Highlights00:00 — “Every business is subject to the laws of physics and math… Execution is the only moat.”03:07 — Stevie on becoming the world’s first female pro gamer and how competitiveness fueled her career.06:25 — The undeniable product-market fit that convinced Stevie to join Vanta.14:02 — Facing 40+ copycat competitors and learning that flashy marketing can’t beat sustainable growth.16:23 — Transitioning from transactional selling to deep, value-based discovery using MEDDPICC.18:30 — Creating Vanta’s “CIA” Competitive Intelligence Agency to win back customers.26:10 — Launching the experimental enterprise sales team and the patience it took to scale it.47:08 — Rebuilding post-sales into separate customer success and account management functions.50:56 — Vanta’s next big GTM bets: platform sales, public sector, and deeper enterprise expansion.53:27 — How Stevie is using AI in revenue operations and her own work life.Guest LinksLinkedIn: https://www.linkedin.com/in/steviecaseThanks to our Sponsor: QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Gaurav Agarwal is the COO of ClickUp, where he’s helped scale the company 17x in two years and cut CAC by 3x—all while leading across marketing, product, sales, and services. Formerly in banking and product roles, Gaurav brings a rare systems-oriented mindset to growth. He’s known for connecting the dots across GTM, scaling PLG engines, driving incrementality with rigor, and building cultures of experimentation, ownership, and speed.Discussed in this episodeWhy growth is more about systems than marketingHow ClickUp scaled 17x while reducing CAC by 3xThe cultural shifts required to align GTM teamsIncrementality testing vs. attribution modelingBuilding a true sales motion on top of PLGInput KPIs as a driver of experimentation speedHow ClickUp is using AI across marketing and salesThe concept of GTM as demand creation vs. harvestingEpisode Highlights00:00 — Everyone is doing all the work—but you're winning by chance, not by design02:01 — Gaurav on seeing growth as a systems function, not just marketing13:33 — Culture alone delivered roughly half of the 3× CAC reduction at ClickUp15:53 — Gaurav defines incrementality testing vs. flawed attribution models29:27 — Setting input KPIs so squads deliver a “win every week” keeps momentum high32:53 — AI is being embedded across PLG + GTM workflows—from content briefs to deal signalsRecommended BooksShareholder Letters by Jeff Bezos ReferencedClickUp:https://clickup.com/• Gong: https://www.gong.io/• Netflix: https://www.netflix.com/• Robinhood: https://robinhood.com/Guest Links (Gaurav Agarwal):LinkedIn:https://www.linkedin.com/in/gauravragarwal/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTMnow Podcast (on all major directories): https://gtmnow.com/tag/podcast/Thanks to our Sponsor: QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

John Fernandez is SVP at Datasite, with a track record as GTM leader at Glia, ContentWise, and Diligent, having scaled teams through IPOs, acquisitions, and $1.4B in equity events. At Glia, John pioneered revenue marketing’s impact, driving 71% of pipeline and 60% of new business revenue from marketing. Connect with him for real-world GTM lessons, scaling playbooks, and unique frameworks for aligning marketing with revenue.Discussed in this Episode:How to architect a B2B marketing org that is truly accountable for pipeline and revenue, not just “influence”Aligning product, content, and campaign teams to ONE goal: pipeline creation (culture, incentives, and operations)The “Value Chain” framework for mapping marketing’s full-stack impact across the GTM engineJohn’s “4 Whats” Framework for operationalizing measurement: what's working, what's not, what's new, what's nextWhat’s broken about attribution today and why multi-touch measurement is often a red herringThe shift from SEO to GEO: How generative AI is re-writing digital discoverability and B2B content strategyAI in marketing without losing authenticity: human-in-the-loop, voice, and trust factors you need to watchWhy more Martech isn’t the answer (and the tech stack crisis facing GTM teams)Deep problem understanding as a GTM superpower (what chess can teach SaaS leaders about winning)Key moves for founders and GTM leaders facing today’s attention and signal problemGuest Speaker Links (John Fernandez):LinkedIn: https://www.linkedin.com/in/johnfernandez/Datasite: https://www.datasite.com/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://substack.com/@sophiebuonassisiWhere to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Erica Anderman is the co-founder and COO of Foodini, an AI-powered platform solving food allergy and dietary transparency through data infrastructure. With over 15 years of go-to-market experience across foodtech and vertical SaaS, Erica has led revenue at companies like Slice, Seated, and Odeko, and held roles across sales, customer success, partnerships, and RevOps. She began her career in door-to-door restaurant sales and now builds GTM from the ground up, helping 50% of the population with dietary needs find safe, personalized dining experiences.Discussed in this Episode:Transitioning from CRO to founder (and why it’s so humbling)Tactical frameworks for finding product-market fit (especially in early pivots)Building a GTM motion from zero using community and customer obsessionWhat AI actually changes in GTM (hint: it’s not just about productivity)How to treat fundraising like a sales motion (including identifying your ICP)Practical tools Erica is using to build GTM motions faster with fewer resourcesHighlights:00:45 From Sales to CRO: The Unconventional Path02:47 Why Being a Generalist Can Make You a Better Leader05:31 What AI Is Really Doing to GTM Roles06:33 Scaling Yourself Before You Scale Your Team08:00 From CRO to Founder: Sales Skills That Transfer to Fundraising10:10 Fundraising Is Just Another Sales Funnel14:12 Relationships Compound in GTM and Fundraising22:33 Finding PMF by Listening Hard26:04 When Your GTM Motion Becomes Compliance-Driven27:41 Community as a GTM Lever (Not Just a Buzzword)38:28 Pre-PMF vs. Post-PMF42:53 Turning Messy Data into Valuable Content56:12 Tools Over Headcount: Erica’s Favorite AI StackGuest Speaker Links (Erica Anderman):LinkedIn: https://www.linkedin.com/in/ericaandermanFoodini: https://foodini.co/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/insophiebuonassisiNewsletter: https://substack.com/@sophiebuonassisiThanks to Our Sponsor – UserEvidence:UserEvidence is the Customer Evidence Platform that helps you collect feedback, surface proof points, and turn customer wins into bite-sized assets your sales and marketing teams can actually use. Capture social proof at scale. Arm reps with credible stories. Close more deals with trust.Learn more at: https://userevidence.com/gtmnowWhere to Find GTMnow:Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

This bonus episode explores one of the most important shifts happening in go-to-market right now: the move from optimizing for humans to optimizing for AI.Mike Walrath, CEO of Yext and former founder of Right Media (acquired by Yahoo for $850M), shares why this change is as big — or bigger — than the first wave of digital transformation. You’ll learn how AI agents are changing how customers discover businesses, why your structured data now matters more than your homepage, and what you can do to stay ahead.This is a clip from the full episode with Mike — a must-watch roadmap for the AI-driven future of marketing. Hit the links to dive into the full conversation.• GTMnow: https://gtmnow.com/gtm-146-future-of-search-ai-digital-presence-mike-walrath/• Apple: https://podcasts.apple.com/in/podcast/gtm-146-the-future-of-search-ai-and-digital/id1369291464• Spotify: https://open.spotify.com/episode/2xs4xXGmTTKXHSNUMmYqvy• YouTube: https://www.youtube.com/watch?v=4m1051j_hq4&t=1332sThanks to our Sponsor: QualifiedPiper is the #1 AI SDR on G2.AI SDR agents are changing the future of sales. And Piper is leading the way.Piper is the top-ranked AI SDR on G2, trusted by hundreds of high-growth GTM teams — including many in the GTMfund community. She works around the clock to follow up with every lead, book meetings, and qualify prospects, all by reading real buying signals.That means your team spends less time chasing and more time closing.Piper isn’t just automating repetitive work — she’s transforming pipeline generation at scale.Discover how AI SDRs like Piper can help you build pipeline faster at qualified.com.Visit us: https://gtmnow.com/Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow/Follow us on Twitter/X: https://x.com/GTMnow_The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Doug Camplejohn is a serial entrepreneur and seasoned executive with extensive experience in B2B SaaS and go-to-market strategies. He has previously held leadership positions at major tech companies including LinkedIn, Salesforce, and Apple before founding Coffee, an AI-first CRM platform.Discussed in this Episode:AI-powered CRM and sales automationGo-to-market stack optimization and simplificationBuilding and scaling B2B SaaS companiesRevenue operations (RevOps) and AI integrationSerial entrepreneurship and company buildingTransitioning from big tech to startup founderHighlights: 04:35 From Fliptop to LinkedIn: how Doug navigated acquisition and scaled Sales Navigator.06:33 Why Sales Nav was a $250M business with a “crappy product” — and how Doug turned it around.09:56 Doug’s “awesome test” for hiring top talent (and the 90-day rule he swears by).13:26 The speed dating hack that landed Coffee’s first sales leader.17:36 What Doug learned running Sales Cloud at Salesforce — and why he left.22:22 The biggest missed opportunity inside Sales Navigator (and what he’d do differently).24:37 Why sales tech stacks are bloated — and how AI-native CRMs solve it.28:36 What makes a true AI-native product (and why Coffee is built different).31:36 The Rippling-inspired vision behind Coffee’s GTM strategy.34:47 Three versions of Coffee — and why reps are swiping their own cards.39:44 AI agents vs. simple automations — what the future actually looks like.42:41 Why SDRs won’t disappear — but their job will change.47:45 Data as the new moat: how to build durable product advantage in the AI era.50:08 Why Doug runs a podcast and thinks every startup should act like a media company.55:09 The new math of headcount: scaling to $100M+ with fewer hires.56:45 The “TAM is dead” take — and how Doug thinks about modern segmentation. Guest Speaker Links (Doug Camplejohn):LinkedIn:  https://linkedin.com/in/camplejohnCoffee: https://coffee.aiPodcast: https://www.coffee.ai/podcastHost Speaker Links (Sophie Buonassisi):LinkedIn: https://linkedin.com/in/sophiebuonassisiNewsletter: https://substack.com/@sophiebuonassisiThanks to our Sponsor: TriNetEvery early-stage founder is told to focus on product and growth. But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey.“Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth.  Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical. TriNet exists to make that easier. TriNet’s full suite of HR solutions is designed to support companies at critical inflection points – from early traction to scale. Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_ YouTube: https://www.youtube.com/@GTM_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content. 

Austin Hughes is the founder and CEO of Unify, a platform helping high-growth teams turn buying signals into pipeline. Previously, Austin led the growth team at Ramp, where he scaled the org from 1 to 25+ and pioneered a product-led, experiment-driven GTM approach. With a background in investment banking and venture capital, Austin brings a uniquely analytical and first-principles mindset to modern B2B growth.Discussed in this Episode:Why you should run marketing like productDistribution is a startup's best friendHow Austin’s content strategy turned LinkedIn into a hyper-efficient channelWhy the best growth hires today are ex-engineers or investorsHow AI is redefining go-to-market motionsHighlights: 04:00 Ramp’s growth org: running 100+ experiments per quarter08:45 Why LinkedIn became Unify’s silver bullet11:30 Austin’s content creation workflow (and why he doesn’t use AI to write)13:00 Technical vs. traditional growth marketers—how to hire for impact17:00 Using Unify to merge 1st & 3rd-party data into a signal pipeline20:30 How automation + human-in-loop GTM creates leverage24:00 Austin’s Carta example: what perfect relevance looks like27:00 What broke in outbound and why signal-based selling is the fix32:00 When startups should start ingesting signals36:30 Culture of experimentation: “failure is just a data point”39:00 How Unify is using AI internally for GTM and support ops43:00 What’s coming next: AI-relevant messaging, BDR collaboration tools47:00 The end of traditional marketing roles—and what comes nextGuest Speaker Links (Austin Hughes):LinkedIn: https://www.linkedin.com/in/austin-t-hughes/Unify: https://www.unifygtm.com/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://substack.com/@sophiebuonassisiWhere to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: /@gtm_nowThe GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/Thanks to our Sponsors: TriNetFounding a company is hard enough. Navigating payroll, benefits, and compliance shouldn’t slow you down. That’s where TriNet comes in. They work with startups and scaling businesses to help take HR off your plate, so you can stay focused on building product, growing revenue, and hiring great people - the go-to-market engine. B2B companies like Hivebrite and Equilend trust TriNet to help handle the infrastructure of their workforce, so their teams can focus on execution. Sponsor Link: The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.