In this minisode, we hear from Lou Shipley, a three-time CEO, Harvard Business School professor, and author who has spent his career building and scaling venture-backed companies. This clip focuses on a critical mistake early-stage founders make: delegating sales before they truly understand the problem they’re solving. Lou walks through how he validated a company by getting directly in front of customers, why founders have to act as the first salesperson, and how real product-market fit only em...
Jun 21, 2026•14 min
Enterprise AI buying has moved quickly, but durable adoption still depends on context, security, workflow fit, and measurable business impact. Daniel Simon, Enterprise Account Executive at Glean, joins John Kaplan and John McMahon to discuss what it takes to sell AI in complex enterprise environments, why multi-threading matters more when buyers are evaluating broad organizational change, and how strong sellers build trust by tying use cases to productivity, governance, and ROI instead of relyin...
Jun 18, 2026•1 hr 2 min
In this today’s segment, Dan Sperring, founder and CEO of Align ICP, breaks down a mistake most revenue leaders make when defining their ideal customer profile. The instinct is to chase the highest lifetime value customers, but those segments are often the hardest to win, the slowest to close, and the first to break when the market shifts. This clip focuses on how to balance three critical factors inside your ICP: lifetime value, ease of acquisition, and market health. Dan explains why ignoring ...
Jun 14, 2026•11 min
Consumption pricing and AI adoption are forcing revenue teams to prove value faster, with less room to hide behind contracts, pilots, or broad technical promises. Seong Park, Senior Vice President of Customer Support and Services at Cursor, joins John Kaplan and John McMahon to examine how customer success has become a consultative, technical, and commercial function in modern go-to-market. The conversation explores why post-sale execution is now central to retention, how teams need to embed int...
Jun 11, 2026•1 hr 2 min
Doug Holladay shares a powerful personal story of forgiving someone he resented for 35 years after an unexpected encounter at a college reunion, emphasizing that forgiveness is fundamentally about personal work rather than the actions of others. He discusses the distinction between forgiveness and reconciliation, stressing the importance of releasing expectations for perfect apologies and instead focusing on recognizing sincere intent in others' gestures. The episode concludes with practical gui...
Jun 07, 2026•17 min
High-performing teams need trust before the pressure hits. Lindsay Shookus spent 20 years at Saturday Night Live, including 10 years as a producer, where every week required a team of writers, cast members, celebrity hosts, musicians, producers, and crew to create a live show in six days. In this conversation, Lindsay joins John Kaplan and John McMahon to share what SNL taught her about building trust quickly, hiring people who elevate the room, reading talent under pressure, and creating a proc...
Jun 04, 2026•59 min
Sales kickoffs can become expensive calendar events if leaders are not clear on what the gathering is meant to accomplish. In this Revenue Builders replay, John McMahon shares his perspective on how CEOs and CROs should think about SKOs, from motivating the sales force and aligning teams around company goals to delivering training that actually prepares reps to execute. He also explains why peer-to-peer knowledge transfer is often the hidden value of bringing the sales organization together, why...
May 31, 2026•6 min
Enterprise sales breaks down when teams confuse activity with progress, champions with coaches, or product interest with business urgency. Stuart Gwynn, a top-performing enterprise seller at MongoDB, joins John Kaplan and John McMahon to unpack what separates disciplined enterprise execution from deal chasing. Drawing from his path from SDR at Pure Storage to closing the largest deal in MongoDB history, Stuart explains why discovery is the foundation of value-based selling, how to test whether a...
May 28, 2026•1 hr 1 min
Today’s episode features Sahir Azam, Partner at Index Ventures and former Chief Product Officer at MongoDB, where he helped scale Atlas into a multi-billion-dollar platform. This conversation breaks down what actually separates top enterprise sellers, from intellectual curiosity to resource orchestration, and why those traits alone aren’t enough without leadership building the right operating model around them. Sahir also explains how sales leaders create scale through enablement, accountability...
May 24, 2026•8 min
Revenue leaders are under increasing pressure to grow without adding headcount at the same rate, and AI is forcing a deeper conversation about productivity, consistency, governance, and organizational design. Alex Bilmes, CEO of Endgame, joins John Kaplan and John McMahon to discuss what his team learned from analyzing more than 30,000 real AI workflows across go-to-market teams. The conversation moves beyond tool adoption and into the harder leadership questions: how to create a centralized int...
May 21, 2026•59 min
Consumption pricing puts pressure on the forecast in places traditional SaaS models rarely exposed. Total usage may be easier to model from the CFO’s seat, but the field still has to answer harder questions: which customer, which channel, which rep, and when. In this replay segment, Devavrat Shah explains how AI can help teams learn across cohorts, spot patterns in uneven data, and create more trust in a forecast that would otherwise depend on isolated judgment calls. Devavrat Shah is an MIT pro...
May 17, 2026•6 min
High-stakes sales puts pressure on the mind before it tests the deal strategy. Reps and leaders have to stay present through judgment, rejection, complex stakeholders, and the weight of the number. Dr. Michael Gervais joins John Kaplan and John McMahon to unpack FOPO, the fear of other people’s opinions, and its impact on executive presence, listening, trust, and decision-making. Drawing from his work with Olympians, world champions, Fortune 100 leaders, and elite teams, Dr. Gervais explains how...
May 14, 2026•1 hr
In this segment, Marcy Stoudt, Founder of Revel Companies, breaks down how AI is changing one of the most important responsibilities in sales leadership: coaching. This conversation focuses on a simple but critical shift. For years, managers struggled to observe real customer interactions and give meaningful feedback at scale. With AI, that constraint is gone. At the same time, leaders are dealing with constant meetings and cognitive overload. Marcy explains how top operators are using AI not ju...
May 10, 2026•10 min
Pipeline generation breaks down when sales organizations rely on individual performance instead of building controlled, repeatable systems. In this episode, Greg Casale shares how his background in engineering shaped a system-first approach to sales, applying principles of process control, data capture, and structured training to reduce variability and improve consistency. The conversation explores why outbound phone remains a critical channel despite its difficulty, how over-automation has satu...
May 07, 2026•1 hr 12 min
Strategic accounts expose where most sales approaches break down, especially when technical capability fails to connect to enterprise-wide value. In this replay segment, Jane Thompson unpacks what it actually takes to navigate complex, multi-division organizations, from building aligned champions to translating solutions into outcomes that matter at the board level. The conversation highlights why intellectual curiosity, multi-threaded engagement, and disciplined account mapping remain non-negot...
May 03, 2026•7 min
AI is shifting from model development to real-world usage, exposing a new bottleneck that most sales teams are not prepared to understand or sell against. As inference speed, memory bandwidth, and infrastructure become the true differentiators, traditional software playbooks begin to break down. Alex Varel joins John Kaplan and John McMahon to unpack what it takes to sell in this new environment, where technical depth, curiosity, and adaptability are no longer optional. The conversation explores...
Apr 30, 2026•1 hr 3 min
Today, a segment from our episode on pipeline generation and building a repeatable revenue system with Christopher Vik, VP EMEA at Samsara and former CRO at Leapwork. In this clip, Chris breaks down why most pipeline generation efforts fail before they even start. He explains how preparation drives conviction, why reps avoid pipeline when they lack insight, and what leaders must do to build a culture where execution actually sticks. If you’re trying to improve pipeline performance or develop mor...
Apr 26, 2026•13 min
PLG can create explosive growth, but it can also mask fundamental gaps in execution, capacity, and long-term durability. As AI-native companies scale at unprecedented speed, revenue leaders face a new tension: how to convert bottom-up adoption into enterprise value without breaking the system that fueled growth. Brian McCarthy joins to unpack how Cursor is navigating this shift, why sales execution becomes the moat in a world of swappable technology, and what it takes to build a go-to-market mac...
Apr 24, 2026•55 min
Preparation does not become less important as sellers gain experience. It becomes more visible as a differentiator. In this replay segment with John Rowell, he breaks down of how disciplined pre-call preparation sharpens positioning, turns cold outreach into meaningful engagement, and allows reps to stay fully present in the moment. The conversation highlights why preparation is not just about information gathering, but about earning credibility, accelerating sales cycles, and creating the condi...
Apr 19, 2026•9 min
Most companies don’t fail because of product, they fail because they never build a clear, repeatable sales system around a problem that actually matters. That shows up early when founders delegate sales too soon, chase broad markets without focus, and struggle to translate technical insight into customer urgency. In this conversation, Lou Shipley brings a career spanning door-to-door selling to leading and teaching at Harvard to break down what separates companies that scale from those that stal...
Apr 16, 2026•1 hr 3 min
Today, we’re revisiting a segment from our episode on selling enterprise software and connecting technical capabilities to business outcomes with John Donnelly. John is a seasoned enterprise sales leader with deep experience scaling complex sales motions across organizations like MobileIron and Kana. In this clip, he breaks down why so many sellers default to features, where discovery goes wrong, and how the best reps connect technical differentiation to real business impact to win complex deals...
Apr 12, 2026•8 min
Most revenue teams believe they have a definedIdeal Customer profile (ICP), but the reality is far less precise, with the majority of pipeline often sitting outside the segments that actually drive retention and expansion. This disconnect creates inefficiency across marketing, sales, and customer success, and is only amplified by AI-driven outreach that scales poor targeting. Dan Sperring, founder and CEO of Align ICP, breaks down why ICP must evolve from a static definition into a dynamic opera...
Apr 09, 2026•1 hr 7 min
Today, we’re revisiting a segment from our episode on Product-Led Growth and modern sales playbooks with Dan Fougere. Dan is the former Chief Revenue Officer at Datadog and former Head of Global Sales at Medallia, now advising high-growth startups. In this clip, Dan breaks down why traditional sales playbooks fail in PLG environments, and how leaders need to shift toward usage-based signals and first principles thinking. He explains how buyer engagement now starts inside the product, what those ...
Apr 05, 2026•7 min
High-growth companies demand constant reinvention, yet most leaders underestimate how deeply roles, go-to-market models, and buyer behavior evolve over time. This episode explores what it actually takes to adapt at that level, from navigating internal resistance to aligning product and sales with how customers truly buy. Sahir Azam brings a rare operator-to-investor perspective, unpacking the realities of PLG to enterprise transitions, the cultural discipline required to scale sales, and how AI ...
Apr 02, 2026•1 hr 7 min
In today’s conversation, former Chief Revenue Officer and private equity operating partner Bob Ranaldi shares why great revenue leaders focus less on static metrics and more on the trends behind them. In this segment, Bob explains why looking at a single month of pipeline or bookings can be misleading, and why CROs and CEOs need to study the progression of key metrics over time. He also breaks down how leading indicators like discovery meetings, pipeline growth, and conversion rates help leaders...
Mar 29, 2026•10 min
If you treat AI as just tech or a tool, you’re likely missing out on the true strategic benefit to your organization. Many leaders are waiting on IT, governance, or the “right stack” while competitors are already compounding gains through faster execution, better preparation, and tighter alignment. Marcy Stoudt returns to unpack why AI adoption starts with mindset, how productivity gains break without cross-functional integration, and why the next competitive edge will come from leaders who driv...
Mar 26, 2026•1 hr 3 min
Today, we're sharing a segment from our episode on leadership, discipline, and relationship-building with Coach John Mosley Jr. Coach Mosley is best known for leading East Los Angeles College and for his role on Netflix’s Last Chance U, where his leadership philosophy is on full display. In this particular conversation, Coach Mosley breaks down a simple but often overlooked principle: rules without relationships lead to resistance . He explains why leaders who rely on compliance lose their teams...
Mar 22, 2026•10 min
Many teams are finding it harder to generate pipeline these days. Is this new pipeline reality here to stay? Generating strong pipeline is still attainable — but the winning approach has changed. Most sales teams are running highly individualized pipeline gen tactics, without the structure, preparation, or leadership discipline required to sustain it. In this replay episode, Chris Vik breaks down why pipeline fails when it’s treated as an event instead of a system, and how high-performing teams ...
Mar 19, 2026•1 hr 7 min
In today’s segment with Eric Erston, longtime sales leader and CRO of RegScale, Eric shares what separates top-performing sales teams from the rest – from maintaining laser focus on metrics and success definitions, to rigorously qualifying leads based on budget, timeframe, and pain points. Eric emphasizes the critical importance of deeply understanding both the ideal customer profile and the individual persona, including the human motivators behind decision-makers, not just their titles. He also...
Mar 15, 2026•8 min
When the relationship between a CRO and CEO breaks down, the symptoms show up quickly in the forecast, the sales plan, and ultimately the boardroom. Strong revenue organizations avoid that trap by anchoring leadership decisions in shared data, realistic planning, and constant communication. In this replay episode, John Kaplan and John McMahon sit down with former CRO and private equity operating partner Bob Ranaldi to break down what effective CRO leadership looks like from both the operator and...
Mar 12, 2026•58 min
