Revenue Builders

Building a great sales organization has always been difficult, and the pace of AI has only raised the stakes. Chad Peets and Chris Degnan join John McMahon and John Kaplan to share what they're seeing as founders race to build go-to-market teams in one of the fastest-moving markets in software. They discuss why companies overhire, how leaders should evaluate revenue quality, what separates "patrio...

Today’s conversation features Brian McCarthy, President of Global Revenue and Field Operations at Cursor and former CRO at Rubrik, where he helped scale the business from $118 million to $1.5 billion in ARR. In this segment, Brian breaks down the rapid evolution of AI in software development, from simple code autocomplete to fully autonomous agent-driven environments, and what that shift means for...

Many stalled deals do not fail because the solution is weak. They fail because the team moved too fast before the buyer had a reason to care, a sponsor willing to mobilize, and enough confidence to take the risk. Randy Riemersma joins John McMahon and John Kaplan to unpack how false velocity, shallow discovery, and weak executive alignment create fragile opportunities that collapse late. He explai...

Seller productivity is being redefined in real time, and the divide is no longer about effort or experience. In this segment, Alex Varel shares a grounded look at how AI is already reshaping the role, from a RevOps leader training multiple agents in a single weekend to the expectation that sellers will augment their own output. The conversation highlights a growing reality for revenue teams: those...

Revenue growth becomes harder to sustain when leadership relies on a handful of top performers, inconsistent processes, or reactive decision-making. Jason Forget, President and CRO of Cockroach Labs, shares lessons from building revenue organizations from the earliest startup stages through large-scale growth, explaining why sales motions must continuously evolve as companies scale. The conversati...

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 c...

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...

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...

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 co...

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...

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 t...

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-t...

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 hi...

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 mode...

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...

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 tru...

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...

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...

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 explore...

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...

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,...

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 cult...

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 executio...

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 inf...

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 le...