How the Deal was Done | Deal Stories Podcast

Ron Masi - Linkedin Ron spent 10 years selling ink on paper before moving into SaaS in 2015. He built his enterprise game the hard way — through coaches, mentors, and a lot of swing-and-miss — until he had a system for running deals at a level most AEs never reach.This episode is about a deal he's never forgotten. Not because of the size, but because of the execution. Every piece moved on purpose. The research, the internal alignment, the mind maps, the 90-minute demo that didn't show a single feature — it all came together and they walked out knowing they'd won.What you'll take away: How to build a deal dossier that actually changes how you sell, how to run an internal team across a complex opportunity without being in every room, and what it looks like when a demo stops being a demo and becomes a story.On research:"We highlighted every page of the CEO's book. We knew everything about them first."On internal selling:"Some people want to run really fast with you. Some people want to go slow. You have to think about how you're going to set this up."On not connecting the dots for the customer:"Never let the customer have to connect the dots. You need to connect them as much as possible."On the demo:"We didn't show the platform. We told them a story. We maybe clicked on four things. Maybe."On the win:"There was no possible way the people coming next were going to do that."On the feeling:"It's like an energy you don't even understand. Like if you played sports and you're in the zone — the basket was as big as the ocean."People Mentioned:Jamal Reimer — Mega deal coach, mentor to RonBrian Burns — Sales coach, introduced Ron to mind mapping & "map to money"Dennis Sorensen — Mentor, taught Ron how to unpack annual reports & 10-KsMind mapping — Core tool Ron used to organize deal strategy and move pieces as the deal evolved

Scott Knights — Major Account Manager at ProofpointThe EpisodeScott Knights is a Major Account Manager at Proofpoint in Melbourne, managing some of the company's largest enterprise accounts across ANZ.This episode centers on how Scott inherited an account where the platform was "just working" — a comfortable situation that most AEs leave alone — and turned it into a full-scale platform transformation by convincing 30+ stakeholders across a parent organization to adopt a new vision for human-centric security. The account had been running the same Proofpoint deployment since the mid-2010s, nearly a decade without strategic evolution. You'll walk away with a clear picture of how to re-enter a dormant account, build a vision-led business case, and orchestrate internal and external stakeholders without losing anyone along the way.Key Quotes:On the most dangerous thing a customer can tell you: "The first bit of feedback was, hey, everything's great, but there's not really any further opportunity here. And that's kind of really interesting because I think that's the place that AI cannot disrupt." On qualifying out before the customer falls in love with the solution: "I said, look, we can definitely solve this. But it's going to cost approximately X. Are you comfortable and confident that your executive or senior leadership are going to sign off on this? And in the end, you could sort of see that that particular individual hadn't kind of really thought through the commercial value of what they were trying to achieve."On what the job actually is: "It's as much of a orchestrator as it is as a technology evangelist. If I look at one of my customers, there's 30 odd stakeholders within the parent org — from security and strategy and architectural teams, through to operational teams, through to legal and vendor managers and procurement."On the culture that quietly kills deals: "If the culture between teams kind of goes a bit off and starts to become even a little bit dysfunctional — people getting agitated with one another, blame or frustration being vented on calls — the wheels can very quickly fall off after that."On what to do when a stakeholder pushes back: "Seek first to understand and then be understood. What's going on for that person? What's the concern? What's the gap they're trying to solve for? And then once I understand that, I can go, okay, well, how do we solve this together?"On the mindset behind everything: "I'm just a very average guy. There is nothing exceptional about who I am or what I bring. But it's determination or diligence or just putting in that little bit of effort every day — it adds up. The success is just a natural outcome of that value creation."Referenced in the episode:Strategic Coach — Dan Sullivan's entrepreneurial mindset framework; Scott studies his work extensively — strategiccoach.comEat That Frog! — Brian Tracy — tackling your single most important task first; Scott keeps this on his deskThe Dip — Seth Godin — when to push through hard seasons and when to move onBooks by Kazuo Inamori — Founder of Kyocera; philosophy of asking "what is the right thing to do as a human being?" in every business decision; most titles in Japanese, English translations availableServant Leadership — Robert K. Greenleaf — Scott's explicit North Star for how he approaches customer relationshipsEnterprise Sales Community — Founded by Jamal Reimer; global network of senior enterprise sellers — referenced as transformative to his own careerConnect with Scott: LinkedIn — Scott Knights, Major Account Manager, Proofpoint, Melbourne

Episode Speaker Notes: Merel Roest — Head of Sales at Guardey, Founder @ Blackbird GTMThe Episode:Merel Roest spent her first five years in marketing before moving into enterprise sales — and that background became her edge. At Freshworks, she closed a three-year, group-wide customer service transformation deal with a 5,000+ employee American organization, selling a product that wasn't fully built yet.Getting to yes meant running two parallel sales motions at the same time: one across multiple client stakeholders all the way up to their CEO, and one internally — working level by level through a hierarchical American HQ she could barely get face time with from her satellite office in the Netherlands. She won both.Now Head of Sales at Guardey, Merel is building the sales org from the ground up — rewriting the pitch, cleaning the CRM data, and using custom-built GPTs to accelerate her team's learning curve.What you'll take away: How to build a deal story that actually lands, how to run an internal sale when the product isn't ready, and what it really takes to go from President's Club rep to first-time leader.Key QuotesOn ditching the standard deck:"It was me talking at you, not me talking with you. I shaped it completely around them — about solving their problem, not about us."On demos that keep people awake:"A lot of account executives click through buttons. That's where people fall asleep. We created personas — this is your customer, this is their problem, this is how they'd use the tool."On the most powerful moment in any demo:"Based on what you've now seen, how would this help you? Let them say it."On social proof that actually works:"Everyone has a logo slide called 'Our Customers.' I hate it — it says nothing. What problem did you solve for them? That's the story you should focus on."On conviction in the deal:"I already knew from my gut from the beginning — I don't know why, but I just felt it. This one's ours."On product belief as a prerequisite:"I would never be able to sell something I don't feel is actually going to help. Your product needs to be good."On the internal sale:"I didn't just have a pitch deck for the customer. I had a pitch deck for our internal stakeholders — one for my line of reporting, one for the solution engineers. Everyone needs to know the ins and outs of why we think this could work."On sales culture:"If your employees are happy, your customers are going to be happy. Culture is very underestimated in high-pressure SaaS sales environments."On moving from rep to manager:"I wanted to earn this person's respect before going into coaching mode. And I told him: I'm going to make mistakes. If I do something that doesn't sit well with you, I hope you'll tell me."On perfectionism at a startup:"Done is better than perfect. I have to tell myself that every single day."Resources & LinksReferenced in the episode:Winning by Design — Jaco van der Kooij's demo methodology; Merel cites his video on keeping buyers engaged throughout a demoThe Maverick Selling Method — Brian Burns — top performers throw out the standard scriptSPIN Selling, MEDDIC, SPICED — frameworks Merel used to build custom GPTs for her team's discovery and coachingTrustPilot & Google Reviews — used by Merel to benchmark client performance and build compelling before/after storytellingGlassdoor — recommended for vetting a company's culture before accepting a roleConnect with Merel:⁠LinkedIn — Merel Roest⁠

Mike Sullivan is Executive Director of Sales at TriNetX, where he sells into top-20 pharmaceutical companies. This episode centers on his career-defining deal - a $3.55M ARR, two-year enterprise contract with a Fortune 500 pharma company that took nearly two years to close, ran 20+ use cases across 5 business units, and required Mike to get high in the account at month 20 of 24.This came at a time of great personal challenge and difficulty - balancing debt and obligations, while threading the needle of an incredibly difficult strategic sale. This deal flies in the face of almost everything we're taught in enterprise sales — and it worked because Mike refused to take shortcuts. He was 39 years old with $80K in debt when he joined TriNetX. This deal changed everything.Connect with Mike:LinkedIn: ⁠Mike Sullivan⁠Website: ⁠mikesullivan.co⁠Mike offers free 30-minute coffee chats for anyone navigating sales challenges or working to turn things around — reach out directly on LinkedIn or via his site.On getting high in the account:"I wasn't high in this deal until month 20 of 24. That goes against everything we're taught in enterprise sales — but I couldn't get there no matter what I tried."On running the pilot:"Rather than you as the customer pointing and clicking, we ran the use cases in our software for you and presented back the output. We did the upfront heavy lifting ourselves."On co-creating the business case:"We were building the business case with the customer throughout the entire deal cycle. So when we had the readout meeting, it was crystal clear — here's where you are today, here's what tomorrow looks like."On commission breath:"If you're making it about you and your commission check, you're putting your deal at risk. You'll subconsciously say the wrong thing at the wrong time."On patience:"Aggressive patience. You've got to be aggressive in the right way — persistent, following up — but patient as hell. If you squeeze an egg too hard, it breaks."On the internal sale:"A lot of times the internal sale is harder than the external sale. We know in our gut which deals have huge potential even when the pipeline doesn't reflect it."On transformation:"I didn't feel like I was selling at all during that deal cycle. It was more just project management — co-creating the process, co-creating the business case, really partnering with them."On mindset:"It's you against you. Are you doing the best you can do every single day? You can only control your attitude, your actions, and your effort. Literally nothing else."Books mentioned:The Gap and the Gain — Dan Sullivan & Dr. Benjamin HardyThe Four Agreements — Don Miguel RuizEgo Is the Enemy — Ryan HolidayTake the Stairs — Rory VadenConnect with Mike:LinkedIn: Mike SullivanWebsite: mikesullivan.coMike offers free 30-minute coffee chats for anyone navigating sales challenges or working to turn things around — reach out directly on LinkedIn or via his site.

Kish Patel: Closing an Eight-Figure Deal in 27 DaysKish Patel is a Strategic Director of Accounts with 15 years in enterprise selling, the last five in cybersecurity and confidential computing. In this episode, he unpacks how he displaced a seven-year incumbent — who was also that competitor's number one customer — and closed a multi-year, eight-figure contract in 27 days. The key wasn't the product. It was financial intelligence, executive alignment, and a two-line proposal engineered directly to the CFO's bonus metrics.Sell the financial gap, not the feature. Kish spent 30 days researching the account before a single pitch — mapping EBITDA pressures, analyst questions, and hiring signals to understand what the business actually needed to achieve.Use the DEF 14A. Pull executive comp structures from public SEC filings and build your proposal around the two metrics that drive their bonuses. The CFO opened the DocuSign and signed in 30 seconds.Orchestrate from the outside in. Kish connected his Morgan Stanley team to the prospect's banking team to create legitimate pressure before ever getting in front of executives. The intro came with weight.AI is the trailer, not the movie. Use AI tools to accelerate research, but listen to the earnings calls yourself. You'll hear what the execs are proud of, what they're dodging, and what the analysts keep hammering — none of which shows up in a summary.Solve bigger problems, close bigger deals. If you're closing six-figure deals, you're solving seven-figure problems. Find the eight-figure problem and your deal sizes follow.BooksThe JOLT Effect — Matt Dixon & Ted McKinnonBrutal Truth About Sales — Brian BurnsToolsWhyzer - Incredible deep research platform, geared toward financial fluency NotebookLM — Google's AI research tool; used to synthesize job postings into tech stack diagrams and generate audio summaries of analyst reportsGemini Deep Research — Used for comprehensive account research before uploading to NotebookLMSEC EDGAR — Search DEF 14A proxy statements and 10-K filings for any public companyPeople & Podcasts Referenced:Brian Burns — Brutal Truth About Sales Podcast (treasure map vs. treasure hunt framework)Nate Nasralla — Peer advisor referenced during a pivotal deal moment Fluint.ioLinkedIn — Kish Patel______________________________________________________How the Deal Was Done hosted by Matthew Klingner. New episodes every week.

Bas Pleune is the newly appointed CRO of Garde, and former enterprise seller at ContentSquare where he spent four years transforming a broken, problem-riddled account into one of the company's most strategic partnerships. He didn't win this account — he inherited it. The technology hadn't delivered, the champion was frustrated, and the contract was at risk. What followed was a masterclass in patience, relationship architecture, and systematic enterprise selling.Key TakeawaysThe org chart as a trust weapon. Bas mapped every stakeholder, reporting line, and informal power dynamic across four years. He used it to brief new champions, earn internal credibility, and open doors into parts of the organization he hadn't reached yet.Align your internal team to their own KPIs. SDRs are measured on number of opportunities — so give them ten smaller ones inside one account. CSMs want multiple active users — so expand the footprint. Pre-sales wants to close — so bring them in strategically. Make it easy for everyone to win by helping you.Use the buying process as a competitive weapon. When champions mentioned evaluating competitors, Bas asked one question: are they registered vendors? He knew they weren't. Then he painted the picture of exactly what that procurement process would cost them personally — and offered to save them the trouble.The tag-along close. Found a champion with enough priority and political capital to drive a deal through procurement? Use their momentum to pull through the lower-priority opportunities that couldn't close alone. Bundle them in and move together.Cloud marketplace as a deal accelerator. Routing deals through AWS, Microsoft, or Google marketplaces lets customers draw down on pre-committed cloud spend — unlocking higher discount brackets and aligning IT, procurement, and the hyperscaler rep all at once.Science over art. The best sales leaders — including some who are engineers by training — treat selling as a machine. Curiosity, business acumen, and financial literacy are the inputs. Everything else follows.Resources & People MentionedContentSquare — Digital experience analytics platform: contentsquare.comGuardey — Bas's current company as CRO: garde.comNate Nasralla — Fluint CEO, referenced on emotional storytelling in deals: fluint.ioJohn McMahon — Referenced on the science of enterprise sales, author of The Qualified Sales LeaderBrandt Williams — Guest recommendation, former colleague, seller turned entrepreneurJamie Ritchie — Guest recommendation, top enterprise seller at ContentSquare UKJamal Reimer — Enterprise sellers community, where Bas and Matthew connectedConnectBas Pleune: LinkedIn

Rachit Kataria | The Only Deals Left Are the Human OnesRachit Kataria is co-founder and CEO of Centralize, backed by Y Combinator and Salesforce Ventures. He's a product engineer by trade who built a GTM motion from zero that's now landing enterprise customers like Intercom, Brex, Highspot, LangChain, and Cresta. This episode covers the future of strategic selling in an AI world, how Rachit built Centralize's go-to-market from the ground up, and why the sellers who thrive in five years will look nothing like the ones being replaced today.Key Quotes"Transactional sales might just die in five years. The only moat you have is your relationships.""Enterprise sales is not a meritocracy. Your job is not to get them to say yes to your product. It is to make it the most politically easy thing to say yes to.""I'm just here to get your shit done internally. You want to get something done? I'm just here to make it happen.""We call it relationship amnesia. You don't even realize you have it. And the worst thing is when someone leaves the company and walks out the door with them.""The most important deals worth getting done right now do not happen without crossing a certain trust threshold.""AI gets you to the last mile. You already have the puzzle pieces, you know what to say. With us, you know whom."Main Takeaways & Discussion PointsTransactional sales is being automated out of existence. Rachit's thesis: in five years, AI will handle everything that's copy-paste, template-based, or sequence-driven. What's left is enterprise — complex, human, trust-dependent deals. The sellers who are building those skills now are future-proofing. Everyone else is on borrowed time.Relationship amnesia is costing companies more than they realize. Every rep who leaves takes their relationships with them. Every warm connection sits dormant in someone's inbox. Companies treat their relationship network as a people problem when it's actually an infrastructure problem — and most haven't built the infrastructure.The below-the-line stakeholders will sink you just as fast as missing the above-the-line ones. Going high in the org isn't enough. If the people vetting, implementing, and living with the software aren't on board, the deal dies anyway — just slower and more painfully.The SLG to PLG journey. Centralize started top-down: get the CRO and VP of Sales excited, roll it out. What they discovered is that the best individual reps — the forward-thinking ones closing the most complex deals — were pulling it up organically in QBRs and one-on-ones. One rep at Cresta used it in his session at their sales kickoff. His manager said it was teaching him how to think like an AE before he'd ever run a full sales cycle.The "slopification" of outreach. AI has made every message beautiful and every inbox unreadable. The only way through the noise now is trust, creativity, and relationships — the things that can't be templated. The sellers who understand this are pulling further ahead. The ones still optimizing sequences are running faster on a treadmill.Time to value is the new moat. Cursor, Lovable, Centralize — the companies winning in AI aren't the ones with the most features. They're the ones where a user gets an undeniable "aha" in the first 10 minutes. In B2B, that moment has to exist at the individual rep level before it ever becomes an enterprise conversation.Resources MentionedCentralize — Relationship intelligence and multithreading platform: usecentralize.com (single player mode available — early access via the site)Y Combinator — Centralize went through YC two years ago: ycombinator.comSalesforce Ventures — Lead investor post-YCCursor — Referenced as the benchmark for "time to value" in AI tools: cursor.shLovable — Referenced alongside Cursor as a model for viral B2B product adoption: lovable.devConnectRachit Kataria: LinkedInCentralize: usecentralize.com

Jamal Reimer is one of the most recognized voices in enterprise selling. While at Oracle, he closed three separate $50M+ transactions with major international firms - and has since built a global community, coaching practice, and an AI platform around helping senior sellers engineer deals at that scale. He popularized the term "mega deal" long before it became a LinkedIn buzzword, and his book Mega Deal Secrets tells the unfiltered story of how he closed his first one, coming out of years of mediocrity and missed quotas.This episode covers the mental and tactical shift from run-rate selling to strategic selling, what actually happened inside Jamal's first $50M deal, how the best sellers in 2026 are using AI differently than everyone else, and why financial fluency is now the most underleveraged skill in enterprise sales.Resources: Mega Deal Secrets (Book)Jamal's novel-format account of his first $50M deal at Oracle. Covers the full arc from near-churn to landmark win, including the mindset shifts, internal politics, executive dynamics, and commercial engineering that made it possible.⁠https://www.amazon.com/Mega-Deal-Secrets-Biggest-Career/dp/1737765527⁠Enterprise Sellers Community:A global network of senior strategic sellers focused on closing seven and eight-figure deals. Weekly wins, peer accountability, and shared playbooks. This is the community referenced throughout the episode where members regularly share business cases with eight digits on them and pricing slides that go into the millions. Jamal and Matthew both credit this community as a key accelerant for thinking bigger and borrowing conviction from others who've done it.⁠https://www.enterprisesellers.com⁠WHYZER.aiJamal's AI-powered platform for account research and financial intelligence. Built for enterprise sellers who need to understand how executives are compensated, how companies are structured to transform, and where budgets are actually allocated. The platform operationalizes the financial fluency concepts discussed in this episode, helping sellers see at a glance the metrics that matter to their buyers.⁠https://www.whyzer.ai⁠Financial Fluency Sessions:Jamal runs free sessions on financial fluency for enterprise sellers. This is the skill he identifies as most underleveraged in modern sales: the ability to speak the language of finance, structure proposals around executive compensation metrics, and translate product capabilities into EBITDA impact, margin expansion, or net revenue figures.⁠https://www.jamalreimer.com⁠Connect:Jamal Reimer on LinkedIn⁠https://www.linkedin.com/in/jamal-reimer⁠Guest Background:10+ Years at Oracle: as a Senior Strategic Sales ExecutiveLandmark deals: Three separate $50M+ transactions with major international companiesAuthor: Mega Deal Secrets - a novel-format account of his first mega dealCommunity: Founder of a global community of senior strategic sellers - Enterprise Sellers Current company: CEO & Founder of WHYZER - an AI-powered platform for account research and financial intelligence for enterprise sellers

Sam Quirke used sales to build his dream life (and house) in the French Alps. Then proved record-breaking success depends on dedication to client value and commitment, not location.What started as a narrow proof-of-concept with a major European media company expanded into a career-defining transaction. Over 18 months, Sam navigated 40+ stakeholders, a 500-question RFP, and converted skeptical finance teams—ultimately helping him become Chargebee's #1 global performer.He shares how he builds conviction early, treats major deals like a "prize tree" requiring constant attention, and why the AE-SE partnership was the secret weapon behind his success.Key Tactics & FrameworksStakeholder MappingBuilt a visual stakeholder map in Google SlidesMarked contacts blue (not yet won) or green (thumbs up)Reviewed with champion every two weeks to identify gapsThe AE-SE PartnershipOne-to-one alignment with SE partner BalaClear ownership: AE owns the business problem, SE owns the solutionMutual feedback loops after every callCustomer literally joked about wanting to hire the SE—multiple timesPeer Proof PointsUsed US competitor wins to shift internal appetite for changeLed with company names in outreach: "We work with A, B, and C who are just like you"Avoided formal case studies—name drops carried more weightProspecting PhilosophyHyper-tailored emails with a clear point of view: "I think X is happening, I know Y is in place, so Z is a good reason to talk"Cold calls as intel-gathering: "You might have to make 50calls to get 3-4 quality 60-second conversations"Treats every Tier A account like a long-term project—knows their stack, their history, their triggersKey Quotes: On the turning point:"The biggest shift went from the main risk being changing to Chargebee to not changing at all and sticking with what they had."On champion relationships:"It goes from me convincing them to us convincing the rest of the business."On AE-SE partnerships:"My SE, Bala- it's been a career highlight being partnered with him. The customer made a joke that wasn't just a joke about wanting to hire him. That's how good he is."On maintaining momentum:"I remember very intentionally treating it as what could be the biggest deal of my career. There's always one more thing you can do on this deal."On prospecting:"You can't beat a good, well-crafted, extremely tailored email. A strong point of view of why anything and why now."On control:"A lot more is in your control than you might think. You can impact the sales cycle massively through your management of it."ConnectSam Quirke — LinkedIn (Calendly link in bio)Chargebee — chargebee.com

Danny Higdon, Founding GTM at CoverBase, shares how he closed a transformational deal that tripled his company's revenue. A Fortune 100 healthcare contract that changed the trajectory of both the business and his career. This isn't your typical quota-crushing story; it's a masterclass in enterprise sales execution, strategic patience, and leveraging limited resources at an early-stage startup.Guest Background:Danny Higdon | Founding GTM at CoverBase12+ years in sales: SMB payments → enterprise SaaSPrevious: WorldPay, MX Technologies4 years sober, heavy investor in sales coachingClosed 20+ deals in first year at CoverBase (ranging from $10K to seven figures)About CoverBase: AI-powered vendor risk assessment platform serving highly regulated industriesWebsite: coverbase.aiConnect with Danny: LinkedIn - Danny Lee HigdonResources & Books MentionedBooks"The Obstacle is the Way" by Ryan HolidayEssential for sellers in the struggle—your obstacles are doing the right workTools & PlatformsSuperhuman: Email management (Danny went from 69K unread to inbox zero)Hundred Handshakes: Org chart mapping softwareChatGPT: Conference research, lead generation automationFluint.io / WHYZER: AI sales tools (referenced in context)Coaches & Thought Leaders ReferencedJamal Reimer: Oracle enterprise seller, placed big bets even risking zero yearsBrandon Fluharty: "Steak dinners don't sell transformational deals"—narrative and business cases doAmber Deibert: Brain science in sales—your brain tries to keep you alive, not successfulMatt Stocking: Danny hired him for bi-weekly coaching during this dealNate Nasralla: Founder of Fluint.io Memorable Quotes:"You have to slow down to speed up. You're not going to hit a $1.2M quota closing $60K deals.""Understanding is a privilege of the historian, not the adventurer." "Make a decision that you're not going to give up trying to be good at this.""More people can coach than do. You don't need to replace your job with it—just engage in the act of teaching & growing.""Theory is in the past. When you screw up in a deal and someone says 'you should have done X,' you never forget that moment."Connect & Learn More:CoverBase: coverbase.ai Danny Higdon: LinkedIn (writes about tech sales, sobriety, and fitness)This episode is a reminder that transformational deals aren't won with perfect inbound leads or flashy demos—they're won with strategic patience, relentless curiosity, and the courage to place bets before certainty arrives.

As 2024 comes to a close, and sights set on 2025, Andrew discusses major life updates including his introduction to fatherhood, his growing and evolving consulting business, and the conclusion of How the Deal was Done Podcast plus what is on the horizon.Interested in developing business cases WITH your champions? Checkout Fluint to do just that. Grab a free download of their top performing sales frameworks and templates. And listen to a few How the Deal was Done eps by visiting:https://www.fluint.io/dealpodTimestamps: 02:57 Consulting & Professional Updates06:10 Future Plans and New Podcast Concept for 202509:01 Gratitude and AcknowledgmentsShoutouts:- OrgChartHub: Co-Founders Dan Currin and Austin Birch original supporter and sponsors of How the Deal was Done- Fluint: Nate Nasralla and Ben Wordell current sponsors and partners of the podcast.- Thousands of listeners including over 100+ who have How the Deal was Done as a top podcast- Brett Muni for the support as editor and now Producer of the podcast- Looking for more Sales Podcasts & Content? - checkout Scott Ingram's Sales Success Stories Podcast. https://top1.fm/all-sales-podcast-episodes/

Another special guest host episode featuring Mitchell Kasprzyk. In this episode, Dave Brock shares his unique journey into sales, highlighting the importance of understanding customer needs and building trust. He recounts memorable deal stories, particularly focusing on a young salesperson's success through effective coaching. The conversation emphasizes the significance of continuous learning and adapting sales strategies to meet customer expectations, ultimately leading to successful outcomes. Timestamps: 00:00 Introduction to Sales Journey 03:57 Memorable Deal Stories 11:58 Understanding Customer Needs 20:09 Building Trust and Confidence 27:59 Continuous Learning and Adaptation Resources: David Brock on LinkedIn: https://www.linkedin.com/in/davebrock/ David’s blog: https://partnersinexcellenceblog.com/ David’s book: https://www.amazon.com/Sales-Manager-Survival-Guide-Lessons/dp/0997560207 Mitchell on LinkedIn: https://www.linkedin.com/in/mitchell-kasprzyk-3296b898/ Questions, comments, ideas - reach out to https://www.linkedin.com/in/andrewkappel/

In this episode of the Deal Stories podcast, Vince Beese, a seasoned sales leader with extensive background in sales, shares insights from his career, and focusing on a significant deal he closed with Yahoo. The highlight of this deal is navigating the RFP process, the challenges faced during negotiations, and the importance of alignment and honesty in enterprise sales. Closing it out: Vince emphasizes the need for hustle, persistence, and a clear value prop when closing large deals. Check out SalesHQ next time you are selling/visiting the Raleigh-Durham area! Timestamps: (00:00) Intro to Vince Beese and Sales HQ (02:12) Cheetah Mail Deal Background (04:24) Navigating the RFP: Telling Client What they Don't Want to Hear (08:24) Small Startup - Challenges in Closing the Deal (11:44) Celebrating Success and Reflections (14:06) Key Takeaways for Enterprise Deals Resources: https://www.linkedin.com/in/vbeese/ https://www.saleshq.co Questions, comments, ideas - reach out to https://www.linkedin.com/in/andrewkappel/

Chas Puleo, Senior Sales Executive at Alkami, returns to in this follow-up episode to last week's conversation (Ep. 55) to discuss the closing of a 2-year, $5 million digital banking. He highlights the importance of aligning with the client’s business needs and the role of executive involvement in moving large deals forward. Background: Chas has been a Senior Sales Executive at Alkami for five an years selling digital banking solutions to U.S. financial institutions. The $5 million deal took over two years to close, involved multiple C-suite executives, and was for digital banking solutions. Challenges: The primary contact in the deal was promoted mid-process, requiring Chas to rebuild the relationship with a new champion from scratch. Timing conflicts at a key conference led to difficulties in securing critical face-to-face meetings with the client. Key learnings: Building strong relationships based on trust and transparency is crucial for closing major deals. ​Involving the C-suite early and maintaining their engagement throughout the process can greatly improve your chances of success. Timestamps: (01:12) Keys to success in the deal. (03:40) Positioning yourself as a partner vs. vendor. (06:53) Relationship building with trust and transparency. (08:52) Importance of executive leadership involvement. (14:45) Internal deal briefings and executive communication strategy. (20:15) Challenges of partner vs. vendor positioning. (26:21) Significance of texting in building client relationships. Resources ​Find Chas on LinkedIn Checkout Run the Hills where Chas releases his newsletter Find Chas's art online Thank you to Fluint for Sponsoring this episode They help sellers build a business case that cvan sell for them even when they aren’t in the room.  Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

Chas Puleo, a senior sales executive at Alkami, shares his experience in closing a transformative $5 million deal in the digital banking space. This episode covers the challenges of resetting a deal after a key decision-maker was promoted and the importance of business cases in complex sales cycles. Background: Chas started his career in banking and transitioned into tech sales, currently at Alkami as a senior sales executive. The deal took over two years, with an internal team evaluation for a digital banking platform at a financial institution. Challenges: Rebuilding momentum and trust after the main decision-maker was promoted. Navigating a long, complex sales cycle while maintaining consistent engagement over two years. Key learnings: Building a collaborative business case with the client ensures alignment and trust. Leveraging relationships and offering best practices can help smooth long internal evaluations. Timestamps: 07:15 — Chas's background and entry into tech sales 12:34 — First contact and prospecting challenges 21:10 — The importance of building a champion in the client organization 24:45 — Resetting the deal after a key decision-maker was promoted 31:12 — Collaborative business cases and their importance in complex sales 40:50 — The value of integrity and avoiding negative selling 45:30 — Using imposter syndrome as a superpower Resources: Find Chas on LinkedIn where Chas releases his newsletter Find Chas's art online at Chasisart.com Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room.  Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

Quick episode here. Talking a bit behind the scenes of 'how' the new Leader Leverage Podcast came to be. You can find link to the YouTube of Ep 1 of Leader Leverage Podcast below. Also, you can checkout the new Substack newsletter that goes along with it. Thanks for listening and your support! Link to Leader Leverage Podcast ep 1 now available on YouTube

Starting by handing out flyers in grocery stores, Rob DeSantis worked his way to become a world-class seller, co-founder, and angel investor. Rob is a Co-Founder at Ariba (IPO & Acquired by SAP), early Board Member at LinkedIn, and currently a hands-on startup advisor/investor. Sales has been at the center of his success, and in this interview, Rob shares the most memorable deal and the learnings he has picked up throughout his career. For salespeople, Rob offers advice and tactics that have driven his unrivaled success. For everyone, Rob shares his perspective on how to live a hard-working, happy and purpose-driven life. For Rob, that purpose drives him to continually be a builder of companies, a competitive athlete, and a proud family man and father. Chapter Markers: 0:00:00 - Intro 0:00:39 - Sales Origins 0:16:27 - Ariba Beginnings 0:23:49 - The $10 Million Dollar Phillips Deal 0:41:17 - Money & Time 1:03:53 - Advice 1:13:09 - Legacy A special thank you to Gary Griffith who helped create the opportunity for us to share Rob's inspiring story. Check out the video version of this podcast on YouTube To learn more about How the Deal was Done Podcast - you can subscribe at www.DealStoriesPodcast.com or reach out to host Andrew Kappel on LinkedIn

Check out the Full Length Episode on YouTube where Rob shares the deal stories that standout from his illustrious career so far. Questions, comments, ideas - reach out to ⁠⁠⁠Andrew Kappel on LinkedIn⁠

Mitchell Kaspryzk re-joins the podcast this time as a guest host featuring a discussion with renowned sales expert Andy Paul. Andy shares insights from his extensive career and delve into a challenging deal involving the development of real-time entertainment systems for commercial airplanes, highlighting the importance of trust and understanding in sales. 
 Background: Andy Paul has had a long and diverse career in sales, authoring several books and hosting successful podcasts. 
 The deal involved selling a complex real-time entertainment system to a Fortune 500 media company, which required custom development and cost approximately $12 million. 
 Challenges: The company made a critical pricing error, requiring them to double the cost at the last minute. 
 The deal involved creating a product that didn't yet exist, necessitating true collaboration with the buyer. 
 Key Learnings: Building and maintaining trust is crucial, especially when unexpected challenges arise. 
 Sales success often hinges on deeply understanding the customer's needs and being adaptable in addressing them. 
 Timestamps: (02:37) Andy Paul's entry into sales (05:05) Initial connection with the big media company (08:37) Technical challenges in developing the product (12:21) Critical pricing error and how it was handled (17:18) Importance of the buyer’s experience with the seller (27:30) The value of deep understanding in sales 
 Resources:
 Follow ⁠Mitchell Kasprzyk on LinkedIn⁠ Follow ⁠Andy Paul on LinkedIn⁠Thank you to ⁠Fluint⁠ for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room.  Check out their solution here: ⁠fluint.io/dealpod Questions, comments, ideas - reach out to ⁠⁠Andrew Kappel on LinkedIn⁠

Ian McDonald shares a large deal, where his company first landed the initial product sale, and the process of working hard to make them into a successful multi-product and platform customer .
Background:Ian McDonald is currently an AE manager at Gong with prior sales experience, at LinkedIn and CEB​Ian shares a past deal including the account management tactics used to expand a customer.
Background:​Covers deal setup and the process and relationship development with the AE who won the new logo and the championChallenges:​Aligning customer's needs with Gong's product roadmap​Coordinating with internal leadership to build trust and relationships with the customerKey Learnings:​Focus on being a trusted partner to help overcome speed bumps in the deal cycleKnow the skills that you need and work backwards to develop those skills
Timestamps:(02:00) - Ian's career journey so far(03:15) - Start of the deal(05:40) - Main challenges in the deal(08:15) - Expanding the deal(10:30) - Strategies for getting better(13:50) - Connect with Ian 
Resources:Connect with Ian on LinkedInLearn more about LeaderLevThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: ⁠Andrew Kappel

Episode 50. Thank you for listening this far. More to come!In this episode we welcome Chris Orlob who shares his boomerang journey from seller to startup founder to SaaS sales leader and now back to startup founder. For the deal we cover a recent $110,000 win for his current startup Pclub.io
Background:​Chris identifies more as an entrepreneur than a sales leader, having started his career at InsideSales.com and later founding startups like Conversature and Pclub.io​The deal involved selling Pclub's skill transformation platform to a marketing automation company for $110,000, spanning multiple departments and requiring extensive multithreading.Challenges:​Procurement demanded a significant discount, initially offering a budget far below the quoted price.​Ensuring differentiation and building a strong business case to justify the higher price point against competitors.Key learnings:​The importance of undeniable defensibility, including quantified value, differentiation, and powerful champions.​The value of a multithreaded network and having a compelling event to anchor the negotiation timeline.Timestamps:01:02 – Chris's career journey split across being a seller, leader, and entrepreneur.03:41 – Founding Conversature and its challenges.06:24 – Overview of Pclub's skill transformation platform.08:37 – How the deal started with individual subscriptions leading to enterprise interest similar to PLG model11:03 – Challenges with procurement and the negotiation process.18:48 – Key strategy for successful negotiation: undeniable defensibility.
Resources:Find Chris Orlob on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel


Haley Ben-Izhak shares insights into closing a significant deal with a top home care provider in the US, highlighting the challenges and strategies involved. Background: Haley Ben-Izhak is an enterprise & large account executive for Nevvon; she has a background in advertising sales, event marketing, and is also a business owner. Nevvon is an online training platform for the home care industry Challenges: Long sales cycle over two+ years Various starts and stops and executive turnover Need to align with the client’s budgeting periods and fit into larger software migration a la implementation of a new CRM or ERP. Key Learnings: The importance of multi-threading and engaging with multiple stakeholders early in the sales process. Using Fluint's written business case framework to improve discovery and effectively communicate the economic impact to the client. Timestamps: (0:02:46) Deal OverviewDetails and background about Hailey's company and the end-user client (0:04:25) Challenges in the DealDiscussing the hurdles faced during the sales process. (0:05:57) Integration StrategyHow Nivvon’s software integrates with the client’s systems. (0:08:24) Champion TransitionHandling the transition of the internal champion at the client’s organization. (0:14:09) Utilizing FluentThe impact of using Fluint's business case framework on the deal’s success. Resources: LinkedIn: Hailey Ben-IzhakThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel

Caleb King, a founding Account Executive at Supered, discusses an unusual yet highly successful deal from his time at HubSpot, emphasizing the importance of recognizing and handling outliers in sales processes. The deal involved a large multinational company and was closed in just two weeks. Background: Caleb King was a channel account manager at HubSpot working with agency and consulting partners Now, Caleb also works with HubSpot partners as a Founding Account Exec at Supered. The deal involved a large multinational company, closed in two weeks, and accounted for 95% of Caleb's monthly quota. Challenges: The deal followed no traditional sales or prospecting playbooks. Internal processes and demands for multiple meetings risked slowing down the deal. Key Learnings: Recognize and give special attention to outlier deals. Build a process-driven day but remain open to the unpredictability of sales. Timestamps: 00:56 – Caleb King's background and role at Supered02:59 – Overview of the whale deal from HubSpot04:13 – Selling through the channel and the unique company involved06:07 – Internal operations and managing risk for the deal08:24 – Key learnings from the deal and the importance of process09:49 – Relationship with the rev ops agency involved12:03 – Supered's go-to-market strategy and the concept of the dark funnel Resources: Find Caleb King on LinkedIn Check out Supered Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to: Andrew Kappel

Mitchell Kasprzyk, VP of Sales at Compyl, shares a pivotal deal story that led to a significant funding round for his organization. His journey from opera singer to sales leader adds a unique twist to his approach and philosophy in selling. Background: Mitchell Kasprzyk started his career as an opera singer before transitioning to sales, now serving as VP of Sales at Compyl. The deal involved a significant round of funding for Compyl, initiated through a first call with the CTO of a larger parent organization. Challenges: The CTO's initial resistance, stating he didn't want a sales pitch and wanted to see the tool directly. Overcoming the underdog status of being a lesser-known startup in a competitive cybersecurity market. Key learnings: Demonstrating transparency and empathy can build trust even with initially resistant clients. Understanding and addressing the specific business outcomes and challenges of the client is crucial. Timestamps: 0:00:02 - Introduction and welcome 0:00:26 - Mitchell's career background 0:03:44 - Initial challenge with the CTO 0:06:11 - Networking at an industry event 0:09:34 - Developing the business case 0:15:08 - Key lessons from the deal 0:21:10 - Parallels between opera and sales Resources: Follow Mitchell Kasprzyk on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn

Samantha Price shares her career journey from journalism to sales and details a recent significant deal she closed at Persefoni. She highlights the unique challenges of selling sustainability software to Fortune 500 companies and the strategies she uses to succeed. Background: Samantha transitioned from journalism to sales and now works at Persefoni, focusing on environmental sustainability. She closed a sustainability software deal with a Fortune 500 company; utilizing the Fluint one-page business case to simplify the process by aligning both internal and external stakeholders. Challenges: Selling sustainability software to buyers unfamiliar with purchasing software. Navigating the complexities of budget approval and competitive differentiation in a niche market. Key learnings: Simplifying communication and reducing friction for buyers is crucial. Leveraging relationships and industry connections can open significant opportunities. Timestamps: (0:00:00) - Background of Samantha Price (0:05:27) - Challenges in selling sustainability software (0:07:32) - Insights on understanding buyer's needs (0:10:50) - Strategies for simplifying communication (0:13:19) - Success and replication of the deal (0:14:37) - Benefits of using Fluint to create business cases with your buyers Resources: Follow Samantha Price on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: ⁠fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn

Welcome to a special, non-traditional episode with founder Adam Robinson. His perspectives around organic/social marketing and product lead growth (PLG) have guided the success of his software startups. B2B sellers may learn techniques from Adam's approach to improve his companies' prospecting and sales process execution. Key Topics: Adam's experience with building and growing his companies, including his approach to B2B sales and marketing Adam's use of social media and content creation to drive awareness and build his personal brand The importance of being adaptable and willing to iterate Adam's views on the future of sales and marketing in the B2B space Timestamps: 01:37 - Discussion on sales models and trends, including B2B vs B2C. 02:32 - Contrasting sales models for Retention.com and RB2B. 09:32 - Discussion on PLG and the feedback cycle for experiments. 11:28 - Discussion on the surprises and assumptions in the experiment. Resources: ⁠Follow Adam Robinson on LinkedIn⁠ Check out Adam's Startups: ⁠RB2B⁠ and ⁠Retention.com⁠ Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: fluint.io/dealpod Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

Greg Crisci discusses his unique approach to selling childcare benefits to enterprises, emphasizing the importance of storytelling and business cases. He shares a notable deal that took over 400 days to close, highlighting the challenges and key learnings from the process. Background: Greg is an entrepreneur at heart with a history in startups and a focus on selling products and services that make the world a better place. The deal involved selling a childcare benefit solution to a mid-market company, primarily driven by employee resource groups and the CEO. Challenges: Overcoming HR's perception that childcare wasn't a problem due to lack of direct complaints. Educating the employee resource group champion on how to present the business case effectively to executives. Key learnings: Building a strong narrative and concise business case can drive decisions from the top. Engaging and educating champions within the organization can be crucial for influencing decision-makers. Timestamps: (0:01:12) Greg’s background and entrepreneurial journey (0:04:25) Current role and responsibilities (0:06:46) Explanation of the deal and the solution provided (0:08:54) Challenges faced during the deal process (0:12:38) Importance of a strong narrative and business case (0:17:48) The final steps to closing the deal Resources: Greg's LinkedIn Greg’s podcast Fluint's top five frameworks Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

In this episode, Scott Ingram shares his journey through a significant sales deal that not only secured a world-class client but also exemplified the power of teamwork and cultural values. Scott's experience emphasizes the importance of perseverance, client relationships, and leveraging company culture to achieve remarkable sales success. Background: Scott Ingram is a seasoned sales professional with over 15 years in SaaS sales, and the host of the Sales Success Stories podcast. The deal was with a major digital camera manufacturer and was instrumental in Scott's early career success, highlighting his innovative approach to structuring deals and leveraging company culture. Challenges: The deal faced a critical timing issue, with only days left in the fiscal year to complete the legal review and finalize the agreement. Scott had to convince internal stakeholders and navigate the client's internal processes to get the deal approved under a tight deadline. Key Learnings: The importance of a strong sales culture and rallying internal support can significantly impact the success of a deal. Building deep, personal relationships with clients and working collaboratively can lead to long-term success and substantial lifetime value for the company. Timestamps: (0:01:33) – Scott Ingram's background and career overview (0:03:30) – Introduction to the Sales Success Stories podcast (0:04:20) – The setup of Scott’s significant deal with a digital camera manufacturer (0:07:58) – Key challenges and cultural impacts during the deal (0:12:19) – Scott's critical email and the turning point in the deal (0:19:01) – Celebrating the deal and its long-term impact (0:24:17) – Conclusion and call for top sales performers to share their stories Resources:  Sales Success Media Scott on LinkedIn Scott’s Daily Sales Tip #1529 HTDWD Evan Kelsay's Top SaaS Deal Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell when they aren’t in the room. Check them out at fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn⁠

In this episode of "How the Deal Was Done," Jarred Knapp, an enterprise AE at SPS Commerce, shares his journey from kinesiology to sales success. He details closing a 50k ARR deal in just three weeks using Fluint to build a strong business case. Background: Jarred Knapp transitioned from kinesiology to sales and has been with SPS Commerce for nine years. He closed a 50k ARR deal in three weeks by leveraging Fluint to sell compliance in the retail supply chain. Challenges: Navigating compliance requirements in the retail supply chain. Building a compelling business case that stakeholders can easily understand. Key Learnings: The importance of creating a strong, clear business case. Leveraging tools like Fluint to help you write a compelling business case can significantly speed up the sales process. Timestamps: (0:01:12) - Jarred's background and career journey (0:03:13) - Overview of SPS Commerce and Jared's role (0:03:26) - Introduction to the 50k ARR deal (0:06:04) - Typical vs. accelerated sales cycles (0:08:33) - Importance of compliance requirements Connect with Jarred Knapp on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution and grab the top 5 frameworks by visiting https://www.fluint.io/dealpod Questions, comments, or future guest recommendations- reach out to Andrew Kappel on LinkedIn

In this episode of "How the Deal Was Done," Andrew Kappel and Bijay Alex Mathew discuss a major deal with a leading athleisure retailer facilitated through a key partnership. They explore the challenges faced with outdated software and how over-servicing and strong partnerships played a role in closing the deal. Background: Bijay has 20 years of experience leading sales teams and currently serves as the CRO at Art of Mentoring. The deal involved Art of Mentoring's mentoring software platform and was initiated through a referral by a key partner, targeting a large athleisure retailer with a thousand participants across two programs. Challenges: Demonstrating the capabilities of a new platform while providing access to an outdated sandbox environment. Managing complex use cases and ensuring the reassurance needed for a large-scale implementation. Key learnings: Delivering above and beyond service can differentiate and build trust with clients. Warm introductions and strong partnerships significantly ease the go-to-market challenges. Timestamps: (03:48) Bijay's background leading sellers at big orgs and now international startups plus journey to Austin (07:09) Beginning of the deal: initial contact and importance of the strategic 'thought leader' partner (08:48) Challenges faced with the sandbox environment and platform transition (10:28) Over-servicing to win the deal (13:42) Importance of reassurance and client confidence Resources: Bijay Matthew on LinkedIn Questions, comments, ideas - reach out to: [**https://www.linkedin.com/in/andrewkappel/**](https://www.linkedin.com/in/andrewkappel/)

In this episode, Eric Hamilton, experienced sales leader shares insights on successfully closing a $900k total contract value transaction. And how to navigate a complex deal in the tech industry, emphasizing the importance of customer-centric strategies and teamwork. Background: The deal involved an automotive company, took six months to complete, involved multiple stakeholders from the buying and selling side, and was selling a cloud-based software solution. Challenges: Integrating the new solution within the client's legacy systems. Navigating the complex approval processes. Key Learnings: The significance of forging strong internal alliances and understanding the client's decision-making process. The necessity of being ‘persistently pleasant ‘and resilient during prolonged sales cycles. Timestamps: (00:05:12) Introduction and Eric’s career background and journey in sales (00:08:45) Overview of the deal (00:12:30) Challenges faced during the sales process (00:16:20) Navigating internal processes (00:20:55) Competition and Strategy (00:25:40) Key learnings from the deal (00:30:15) Final thoughts and advice for sellers Resources: LinkedIn: https://www.linkedin.com/in/erichamiltonblueprint/ Book: https://www.thesalesblueprintforsuccess.com/ Instagram: EricHamiltonSalesBlueprint Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

In this episode, Bion Behdin, Chief Revenue Officer of First AML, shares insights into winning a near million-dollar deal in the financial services and regulatory tech sector. Bion highlights the importance of strategic client engagement, internal stakeholder management, and leveraging feedback loops to navigate complex sales processes. Challenges: Securing buy-in amidst global company issues mentioned in the media. Managing internal stakeholder concerns and uncertainties about the deal's feasibility and execution. Key Learnings: Structuring deals with a detailed, proactive approach, including frequent summaries and clear next steps after discussions. Emphasize the importance of top company leaders staying close to client interactions and demos to understand customer needs and address potential challenges effectively. Timestamps: (0:01:44) Background and journey of Bion and First AML. (0:07:16) How the deal was initiated through a chance conversation at a pub. (0:10:24) Advancing through the RFP process and addressing technical requirements. (0:12:11) Importance of involving sales users and navigating internal stakeholder dynamics. (0:16:01) Overcoming challenges amid global company issues and internal concerns. (0:17:42) Learnings from structuring and negotiating large transactions effectively. Resources: LinkedIn: Bion Behdin Questions, comments, ideas - reach out to: Andrew Kappel

Shawn Curtis shares an intense negotiation involving a high-stakes deal at Spreedly, a payments orchestration company. He discusses overcoming internal challenges, strategic decision-making, and lessons learned from pivotal career transitions. Background: Shawn Curtis transitioned from a U.S. Navy career to sales, eventually becoming the first enterprise salesperson at Spreedly. The deal involved a major media conglomerate looking to expand internationally, challenging Spreedly's existing payments infrastructure; it took six months to complete with multiple team members involved in the negotiation. Challenges: Navigating a complex procurement process with stringent and unusual demands from the customer. Overcoming internal resistance and aligning multiple internal stakeholders to meet the deal's requirements and innovate on pricing models. Key learnings: The importance of aligning internal teams and stakeholders to support complex deals. The necessity of maintaining flexibility and openness in negotiations, adapting to unexpected demands and changes. Timestamps: (01:02) Meeting Shawn Curtis and the inception of a pivotal deal. (02:05) Entry into enterprise sales and initial challenges. (05:12) Crucial negotiations and internal alignments. (10:48) Strategic pivot and high-level negotiations with the media conglomerate. (16:04) Critical email and breakthrough in the deal process. (18:29) Finalizing the deal and reflecting on the arduous process. (23:18) Shawn Curtis’s insights on enterprise sales strategies and career growth. Resources: Shawn's LinkedIn RepVue | Sales Organization Ratings, Reviews, Jobs (where Shawn is the Director of Sales) Questions, comments, ideas - reach out to Andrew Kappel

Colin Specter shares his experiencing becoming the top seller at his company and a formative deal that he fell short on and what he learned from it. Background: Colin Specter started his career in SaaS sales at Namely where he became a top 1% seller and progressed to a leadership role now at Orum. The deal involved namely, a tech company specializing in HR software, to the CFO of a large financial services company Challenges: Failing to better understand a company’s broader culture and norms. Facing to check overconfidence when a deal seems to be made already Key learnings: Research and adapt to the corporate culture and expectations of potential clients, especially regarding dress codes. Building a strong relationship with various stakeholders, not just the primary contact, to navigate corporate dynamics effectively. Timestamps: (0:10:25) Immediate Judgment Based on Attire... Colin describes the moment his attire led to a snap judgment by the CFO. (0:13:09) Cultural Missteps and Adaptations... Colin discusses adapting to different corporate cultures. (0:13:56) East Coast vs West Coast Business Culture Differences... Insights into differing business practices between "New York" and "California" businesses and startups. (0:16:47) Building Partnerships and Networks... The importance of building networks and how past connections influence current opportunities. (0:19:23) Learning from Losses... Reflecting on how losses can be more memorable and educational than wins. Resources: Colin's LinkedIn The Nazare Wave  Episode with Ewing Gillaspy Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/Podcast Questions, comments, ideas - reach out to Andrew Kappel

John Barrows, one of the top sales trainers and thought leaders, joins for a look back on his journey and fun discussion on a particularly large and memorable deal from his time at Thrive Networks. Background: John Barrows has 20+ years of sales experience with a variety of companies and as an entrepreneur In this episode he remembers a managed IT services deal he did that was 20x the avg. deal size Challenges: Establishing trust and staying top of mind without being perceived as annoying. Adapting to the evolving sales landscape and shifting from traditional tactics to leveraging technology effectively. Key learnings: The value of playing the long game in sales and building meaningful relationships over time. The necessity of adapting to changing sales environments and leveraging technology to stay competitive. Timestamps: (0:07:28) Reflecting on the challenges faced at a big company versus startups and working on your own (0:13:16) Sharing a specific deal that highlighted the value of persistence and relationship-building. (0:17:14) Utilizing low-tech tactics and the significance of fundamentals in sales. (0:21:20) Discussing the relevance of agility and adaptation in the fast-evolving sales landscape. (0:24:37) Exploring the concept of the infinite game and the importance of aligning with personal values in sales. Resources:John Barrows on LinkedIn The Infinite Game: Sinek, Simon John’s Newsletter John's Podcast Questions, comments, ideas - reach out to: Andrew Kappel

Amanda Brem, founder of the Brem Method, recounts how she pitched and executed her first academic coaching course for pre-medical students, overcoming skepticism and challenges along the way. Through determination and leveraging her strengths, she successfully built a thriving business despite initial uncertainties. Background: Amanda Brem founded the Brem Method, specializing in academic coaching for pre-medical students She secured a deal with a program director to run an academic course for MCAT preparation Challenges: Convincing the program director to take a risk on an unproven product, addressing concerns about potential negative feedback impacting future enrollments. Navigating the complexities of contract negotiations as a small company, especially in contrast to dealing with larger institutions. Key Learnings: Embracing negative feedback as critical feedback to improve and not fearing it as a threat to reputation. Understanding the importance of commitment and follow-through in sales, avoiding second-guessing decisions to ensure success. Timestamps: (0:00) Introduction and background of Amanda Brem and the Brem Method. (5:36) Amanda's experience in sales during her time as a personal trainer and the importance of developing a niche. (7:58) Initiating the deal with the program director and challenges faced during the process. (11:30) Scaling the business and expanding beyond the initial pilot program. (13:18) Sources of information and learning for sales and entrepreneurship. (17:24) Challenges and anxious moments faced during the pitch and contract negotiations. (19:40) Moments of uncertainty and key learning points throughout the deal process. Resources: LinkedIn: [Amanda Brem - Founder - The Brem Method](https://www.linkedin.com/in/amandabrem) YouTube: https://www.youtube.com/channel/UCCs_enSv2UntPXD33e6b6Dg Questions, comments, ideas - reach out to the host: https://www.linkedin.com/in/andrewkappel/

Drew Wills shares his journey from a senior in college struggling to find a job to impressive runs at LinkedIn and Gong and now becoming VP of Sales at Brilliant. Drew emphasizes the importance of networking, leveraging LinkedIn, and sales negotiations. The podcast highlights Drew's approach to renewing a significant deal with a customer by demonstrating indispensable value and learning from past negotiation experiences. Background: •    Drew Wills transitioned from numerous roles at LinkedIn to a leadership position at Gong and now VP of Sales position at Brilliant. The deal, aiming for renewal with a focus on demonstrating value to resist competitive threats. Challenges: •    The rise of the CFO's role in procurement made negotiations tougher, requiring more than just the demonstration of the product's value. •    The shift from growth at all costs to profitability among companies put additional pressure on software services to justify their costs amid layoffs and budget cuts. Key Learnings: •    The importance of building a strong case with the users of the product to ensure internal advocacy during renewal negotiations. •    Clarity on dates and deadlines can significantly impact the negotiation outcome by preventing the extension of discussions beyond the expiration date. Timestamps: •    (0:01:30) Drew Wills intro and career background. •    (0:03:29) Experience and roles at LinkedIn. •    (0:07:51) Discussion on the deal at Gong and the shift in the procurement landscape. •    (0:11:29) Strategies for maintaining price points and demonstrating value. •    (0:17:24) Negotiation tactics and learning from past deals. •    (0:22:38) Drew's new role at Brilliant and the value of corporate gifting. •    (0:25:34) Approaches to sales and business development at Brilliant.Resources: Resources: LinkedIn: https://www.linkedin.com/in/drewwills/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast (http://orgcharthub.com/podcast) Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/ (https://www.linkedin.com/in/andrewkappel/)

Ep. #33 featuring entrepreneur Tom Cates who has a decades long career as a consultant, sales leader, and software founder. Tom got his start in sales with IBM, an MBA from Wharton, moving into management consulting, and eventually starting his own consulting firm and software company focused on B2B business relationships. Background: Tom shares insights on selling high-value B2B products and services and the importance of establishing meaningful, differentiated relationships with clients. The deal story involved a multibillion-dollar IT services client, with the engagement starting around 2017/2018 on a three-year agreement basis, involving a software product aimed at improving client relationships beyond conventional metrics like Net Promoter Scores. Challenges: Showing the client that their success metrics (like Net Promoter Scores) were inaccurate signs of growth and they needed to find new ones. Demonstrating the unique value of their software and consulting services as an unknown entity to a major outsourcer. Key learnings: Getting more customers to promote your product/service revolves around the experience of the "middle" customers (those somewhat satisfied but not fully engaged) rather than focusing solely on detractors or promoters. Success depends not just on delivering value, but also on effectively communicating this value to the right people within the client organization. Timestamps: (0:00:36) Tom Cates intro and background (0:02:06) Acton, Massachusetts where Tom Cates and Andrew Kappel (host) are from (0:04:33) Discussing the lifetime value of a customer (0:06:25) Finding and following your passion (0:09:27) Unpacking the disconnect between high NPS scores and growth (0:15:43) The Christmas tree analogy in sales Resources: LinkedIn: https://www.linkedin.com/in/tomcates/ Tom’s consulting firm: http://www.encompass-cx.com/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Donald Kelly, highlights the challenges and strategies involved in closing a large-scale deal with a school district. Kelly shares insights on the importance of acting as a consultant rather than an order taker and the lessons learned from navigating a complex sales process. Background: Donald Kelly transitioned from various sales roles into the founder of a sales training firm and podcast host. The deal discussed was with a school district, involving document management solutions, taking two years to close, and was valued at approximately $150,000. Challenges: Gaining access to key decision-makers and influencers beyond the purchasing director, and navigating a lengthy and specific buying cycle within the school district. Initially lacking a comprehensive understanding of the client's deep-rooted problems and the need to custom tailor solutions beyond standard offerings. Key learnings: The importance of establishing relationships with key stakeholders and understanding their personal and professional motivations for the deal. Adopting a consultant mindset, focusing on value and impact rather than price, and the necessity of thorough preparation and adaptability in sales strategies. Timestamps: The Sales Evangelist Journey (0:01:41-0:03:41) Overcoming Podcasting Challenges (0:03:41-0:06:19) Navigating a Complex School District Sale (0:06:19-0:11:22) Strategic Planning and Board Approval (0:16:45-0:19:29) Lessons Learned and Wrap-up (0:19:29-0:26:50) Connect with Donald on LinkedIn: https://www.linkedin.com/in/donaldckelly/ Listen to Donald's Podcast here: The Sales Evangelist Donald KellyApplehttps://podcasts.apple.com › podcast › the-sales-evangelist Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Jake Dunlap, CEO and Founder of Skaled Consulting, has worked on thousands of deals, and now he shares his expertise with organizations looking to accelerate their growth. In this episode he recounts a three part deal that grew to $4M in ten months and the sales strategies and philosophies to get there. Background: Jake Dunlap is CEO Skaled Consulting. Has worked on thousands of deals and shares one from earlier in his career that shaped future strategies Key Challenges: Adapting to client budget cycles. Overcoming traditional contract limitations. Navigating enterprise decision-making timelines. Key Learnings: Importance of aligning with client budgets. Using "proof of concept" and "proof of scale" for deal expansion. Flexibility in contracts secures larger partnerships. Timestamps: (1:28) Discussion on Strategic Sales Contracts and Aligning with Client Budget Cycles (6:05) Challenges in Adapting Sales Strategy to Enterprise Decision-making (10:06) Insights on Utilizing "Proof of Concept" to "Proof of Scale" for Deal Expansion (15:04) Jake's Learnings on Flexibility and Customer-Centric Contracts (19:30) Conclusion and Key Takeaways Order Jake's new book at: https://www.jakedunlap.com/the-innovative-seller Find Jake on LinkedIn:  https://www.linkedin.com/in/jakedunlap/ Join the Innovative Seller Community Summit: https://www.jakedunlap.com/the-innovative-seller-community-summit Custom GPTs for Sales: https://skaled.com/insights/custom-gpts-for-sales/ Workshop + Prompt Pro: https://bit.ly/accelerator-and-prompt-pro Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

In this episode Andrew shares a solo deal story from his consultancy: Benchmark Signal Consulting. Other topics mentioned- podcast growth initiatives including the new YouTube channel and some big upcoming guests. Resources mentioned: https://perell.com/essay/imitate-then-innovate/ Episodes Referenced: https://www.dealstoriespodcast.com/episodes/ep-21-special-edition-buyer-se YouTube: https://www.youtube.com/@HowtheDealWasDone Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer relationships. Background on Jesse and the deal: Jesse Woodbury is a seasoned sales professional and Sales Players podcast host The lead came inbound from a UX manager who was reaching out to several vendors Deal Challenges: Initial lack of a clear pain point or urgency from the client's side, making it difficult to push for a substantial commitment. Distinguishing their company from the many other vendors in consideration Navigating the complexities of negotiating an unlimited usage pricing model which Jesse’s company did not regularly offer Key Learnings: The importance of building genuine relationships and having an internal champion within the client's organization can significantly influence the deal's outcome. Creative deal structuring and flexibility in pricing can open doors to larger opportunities and partnerships. Persistence and the ability to adapt sales strategies to meet client needs and internal changes can lead to groundbreaking deals. Timestamps: 0:02:24 - Jesse shares his encounter with Tim Ferriss, showcasing his admiration and the unexpected meeting that influenced him. 0:03:43 - Jesse mentions how Dustin Brown, a mentor and friend, has influenced his approach to enterprise selling. 0:08:45 - The background of the deal Jesse is discussing begins, detailing the initial contact with the UX manager from a large B2C Home Services Company. 0:15:39 - Discussion on the transition of the deal from a small proof of concept to a major project with executive involvement, including strategic outreach and negotiation phases. 0:27:21 - Jesse reflects on the impact of the deal, not just on his career but also on the client's business, highlighting the mutual benefits and the importance of relationship-building in sales. 0:29:35 - Closing remarks from Jesse and Speaker C, with an invitation for listeners to connect and explore further content. LinkedIn: https://www.linkedin.com/in/jessewoodbury/ ‘Sales Players’ podcast: https://open.spotify.com/show/1n4giaqOn4KvM9dk8b6Nm2 Jesse referred by Dustin Brown - link to Dustin Brown episode: https://www.dealstoriespodcast.com/episodes/ep-25-expanding-a-fortune-50-a Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Max Tipton, VP of Sales North America for Paperless Parts, shares the story behind a transformative deal known as "The Earth Mover". Background: A pivotal deal known as "The Earth Mover." The deal was with a major custom part manufacturer in the U.S., aiming to revolutionize their estimation and quoting process. This opportunity was significant for Paperless Parts, marking a strategic push into larger market segments. Challenges: High-Level Engagement: Starting the conversation at the CEO level set high expectations for alignment and delivery. Defining Success Criteria: The client's initial lack of detailed success and technical requirements posed significant hurdles. Build vs. Buy Decision: Convincing the client to choose Paperless Parts' solution over developing an in-house solution. Key Learnings: Executive Bridge Building: Early executive engagement between both companies' CEOs proved critical for trust and alignment. Collaborative Requirement Definition: Working closely with the client to detail their success criteria and technical needs was key. Strategic Patience: The deal required a balanced approach of maintaining momentum while allowing the client time for internal decision-making. Timestamps: 0:00:00 - Introduction and early strategies in deal-making 0:01:27 - Max's journey in sales 0:04:23 - Background on the transformative deal 0:08:09 - Challenges encountered during the deal 0:10:34 - Key strategies used in the deal 0:13:03 - Closing strategies and the role of executive relationships 0:16:23 - Learnings from the deal and its impact on future sales Connect with Max and learn more about Paperless Parts on LinkedIn: https://www.linkedin.com/in/maxtipton/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

In this special episode host Andrew Kappel, and producer Brett Muni reflect on some of the most popular episodes so far, explore how these lessons have impacted Andrew's Sales Consulting Business, and enlist the audience to connect with us on LinkedIn to let us know what content has been the most engaging. Timestamps: 0:01:54 - Discussion on the podcast journey and the milestone of 25 episodes 0:04:29 - Insights on enterprise sales, project management, and the impact of big deals 0:10:30 - Introduction to Benchmark Signal Consulting and the Gong audit and optimization offering 0:12:22 - A look into consulting deals and the project 5000 initiative 0:17:33 - The importance of multi-threading and building a strategic sales pipeline 0:19:12 - Closing remarks and invitation for feedback Connect with Andrew Kappel: https://www.linkedin.com/in/andrewkappel/ Connect with Brett: https://www.linkedin.com/in/brettmuni/ Skip Miller with more train analogies: https://www.linkedin.com/posts/skip-miller-a7243_really-its-about-the-trains-here-i-am-activity-6327423369071464448-dfrQ/?originalSubdomain=uk Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at ⁠OrgChartHub.com/podcast

In this special edition, we hear the buyer and seller perspectives on a $1.2 million deal between Uber Eats and the French startup, OCUS. Host Andrew welcomes Russell Bradley-Cook from HubSpot and Chris Mark, a tech strategy operations expert, to share their firsthand experiences and learnings from this transformative deal. Background: The deal was $1.2m between Uber Eats and OCUS, a French startup specializing in scalable photography services. The seller, Russell Bradley-Cook who currently manages HubSpot partnerships in EMEA, was head of enterprise sales at OCUS. Chris Mark was on the buys side of this deal with UberEats. Chris has directed operations with smaller startups as well as Uber and DoorDash Challenges: OCUS was tasked to build a photographer network in the UK to prove themselves as a reliable vendor to UberEats For OCUS to win they needed to create a seamless API integration between OCUS and Uber Eats' systems OCUS used procurement’s pressure to lower pricing as an opportunity to grow the size of the contract. Key Learnings: Understanding the customer's needs and flexibility can outweigh the scale and resources of larger competitors. Sales executives' understanding of technical aspects, such as API integration, can facilitate negotiations of complex deals. Negotiating a payment structure allowed for cash flow to fund projects before delivery and rapidly scale the business Chris Mark on LinkedIn: https://www.linkedin.com/in/cmark33/ Russell Bradley-Cook on LinkedIn: https://www.linkedin.com/in/russellbradleycook/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Dustin Brown, a seasoned SaaS professional with over 15 years of experience, shares insights from a significant deal with a Fortune 50 company, initially a small 100-user engagement that he expanded to over 1,200 users. Background: Dustin: 15+ years in SaaS, transitioned from small business digital marketing to SaaS platforms. Deal Context: Major deal with a Fortune 50 company, formerly part of Dell, starting from a 100-user engagement. Challenges: Expanding Presence: Limited initial engagement in a large organization (30-40k employees). Operational Complexity: Scaling from small to enterprise-level, integrating with main CRM. Organizational Changes: Navigating pauses and shifts in client’s priorities and structure. Learnings: Relationship Building: Crucial for long-term partnerships, not just immediate sales. Strategic Alignment: Aligning solutions with client’s broader goal to grow from $4 billion to $7 billion in 36 months Continuous Reevaluation: Constantly realigning with client's evolving needs. Sales Philosophy: Sales as an infinite game, focusing on continuous learning and customer needs. Dustin’s LinkedIn: https://www.linkedin.com/in/dustingbrown/ Dustin's New Substack and Podcast: https://diaryofaneliteseller.substack.com/ Resources and Books Mentioned: Selling Above and Below the Line: https://www.amazon.com/Selling-Above-Below-Line-Management/dp/0814434835 How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034/ref=sr_1_1?crid=12VK4VSYJUFV5&keywords=how+to+win+friends+and+influence+people+Carnegie&qid=1707084640&s=books&sprefix=how+to+win+friends+and+influence+people+carnegie%2Cstripbooks%2C148&sr=1-1 Dustin on Scott Ingram’s podcast: https://top1.fm/episode-136-dustin-brown-top-global-account-executive-at-outreach-on-relationships-giving-and-more/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Jeff Kirchick, a seasoned software sales professional and author, relates his experience closing a significant deal with a major healthcare company. Jeff shares insights on the importance of relationship-building, understanding customer needs, and strategic partnerships in the sales process. Timestamps: 0:00: Introduction by Andrew 1:00: Jeff Kirchick joins and introduces himself 2:15: Jeff discusses his background and career in software sales 4:06: Insights on building businesses in various US cities 4:45: Jeff sets up the context of the major healthcare deal 10:30: Discussion on the importance of relationship-building in sales 13:10: Episode wrap-up and ways to connect with Jeff Kirchick Connect with Jeff on LinkedIn: https://www.linkedin.com/in/jeffkirchick/ Check out his award winning book: https://www.amazon.com/Authentic-Selling-Principles-Sales-Everyday/dp/1735956902 Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Rachel Shi, a strategic account executive at Metadata, recounts a complex, 6-figure deal deal with a publicly traded EdTech company. Rachel has varied experience in tech sales, having worked in various roles and organizations, including Hootsuite and Vidyard, and even founding her own startup. Background: Rachel is a Strategic Account Executive at Metadata, with a background in design, founding a startup, and tech sales Rachel successfully got the deal done selling tech solutions to Docebo, a publicly traded Ed-Tech company providing Main Challenges: 8 month sale cycle with over 15 stakeholders Gaining executive sponsorship, dealing with a software approval committee, and convincing a previously uninvolved Google team to support the Metadata solution. Key Learnings: Nurture your champions Creative tactics to your advantage Focusing on aligning product with need Timestamps: [00:01:00] Rachel's career transition from design to tech sales [00:04:00] Beginning of the deal with Docebo [00:07:00] Challenges in obtaining executive sponsorship and committee approvals [00:10:00] Overcoming the final hurdle with the Google team [00:14:00] Securing the deal and post-deal reflections [00:17:00] Rachel's advice on personal development and sales strategy Connect on LinkedIn with Rachel: https://www.linkedin.com/in/rachshi/ Link to Ep from Scott Ingram Pod: Curiosity, Persistence and 100% Ownership with Rachel Shi: https://top1.fm/episode-123-curiosity-persistence-and-100-ownership-with-rachel-shi/ Rachel Shi Post with Recording of her Champion from Deal: https://www.linkedin.com/posts/rachshi_how-metadata-became-famous-in-docebos-gtm-activity-7137812589400461312-h-jf?utm_source=share&utm_medium=member_desktop Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - connect with host Andrew Kappel on LinkedIn: **https://www.linkedin.com/in/andrewkappel/**

Jacob Karp, a seasoned enterprise sales expert with a dynamic background in journalism, media, public relations, and a decade in enterprise sales joins Andrew Kappel for this installment of How the Deal Was Done. The episode delves into a significant deal with a Fortune 200 telecommunications company, revealing Jacob's strategic approach to expanding an existing account, overcoming challenges, and securing successful outcomes. Timestamps: 0:00:30 - Introduction of Jacob Karp and episode overview. 0:01:16 - Jacob's background in journalism and sales. 0:06:16 - Background of the featured deal with a telecommunications company. 0:10:47 - Challenges encountered and strategies employed in the deal. 0:18:10 - Long-term strategies and dealing with detractors. 0:20:12 - Jacob's insights on continuous learning and improvement. Connect with Jacob on LinkedIn:  https://www.linkedin.com/in/jacobkarp/ Find his enterprise sales guide here: https://jacobdkarp.com/revenue/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast

Want to hear a $7-figure deal story where the seller NEVER met anyone at VP or higher? Ever wonder what happens with your slides that you prepare for the champion? Want to learn how to buy something you’ve never bought before and de-risk the vendor race? If so, this is a can’t miss episode about a buyer and seller that did multiple $7-figure enterprise deal to generate 8-FIGURES-WORTH-OF-REVENUE together! This episode features the deal story for an enterprise-level transaction between AltiSales and IBM including both buyer and seller viewpoints. The episode introduces Ewing Gillapsy, a consultant and an experienced buyer with a background in software procurement and IBM, and Tito Bohrt, CEO of AltiSales. Timestamps: Ewing’s Background: (0:01:03) Tito's Background: (0:04:42) Challenges and Deal Setup: (0:07:04) Vendor Competition and Key Learnings: (0:14:49) Deal Impact and Further Discussion: (0:26:16) Connect on LinkedIn with Ewing: https://www.linkedin.com/in/messagemarketfit/ Connect on LinkedIn with Tito: https://www.linkedin.com/in/titobohrt/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - connect with host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/