Revenue Builders

Most SKOs are packed with inspiration and breadth – 30 topics, motivational speakers, CEO talks – but when reps walk out on Monday, they don't know what's different. In this episode, John McMahon and John Kaplan break down how to build an SKO that actually answers the question reps need answered: what do I need to do differently tomorrow?

Key takeaways from this episode: 

Buyers rarely make decisions on logic alone. In this minisode, Randy Riemersma breaks down the six emotions that influence how deals progress and explains why elite sellers know how to create urgency, build confidence, and sustain momentum throughout the buying journey. Randy shares his perspective on the role of fear, curiosity, hope, desire, confidence, and urgency in complex sales, along with why subject matter expertise and genuine curiosity remain essential for earning trust and guiding decisions.

Randy Riemersma is the founder of Sell with Precision, where he helps sales leaders improve execution, leadership effectiveness, a...

Proprietary data, not the software, is the long-term value driver. On this episode, Ann Davis, CRO at Crunchbase, walks through how knowing which customers to pursue drives 2x pipeline growth in six months, why sellers need to stay in control of the conversation, and how she built a headless AI interface that connects Salesforce, Gong, and private market data so reps know exactly what to focus on each day.

Ann Davis is Chief Revenue Officer at Crunchbase, where she leads their shift from product-led to enterprise; she spent five years at Google Cloud running d...

Hiring mistakes often happen when leaders focus on capability and experience without understanding whether a candidate is truly energized by the realities of the role. In this clip recorded earlier this year, Jason Forget, then President and CRO of Cockroach Labs, shares the interview question he uses to uncover long-term fit, why startup environments demand a different type of motivation, and how honest self-assessment can help leaders avoid costly hiring mistakes. The discussion offers a practical framework for evaluating energy, adaptability, and alignment before making critical hiring decisions.

Jason Forget is President and CRO o...

You can have the best product in the world, perfect messaging, and market timing on your side… but if you don't have elite people in your sales organization, none of it matters. Brad Scott has built sales teams at Snowflake, Veza, and now Glean – three of the most different growth trajectories in tech. In this conversation, he breaks down how to hire for the traits that actually predict success: intellectual curiosity, resilience, self-awareness. He also tackles the complexity of selling AI-native products in a market flooded with AI-bolted hype, and why the fundamentals of recruiting, onboarding, and process discipline are...

Most first-line managers are trying to do everything at once – recruit, develop, forecast, and hit their number – all in 62 working days. But Scott Rudy has learned through building teams at high-growth companies that what separates managers who make their number from those who don't isn't effort; it's operating rhythm. In this clip, Scott breaks down how second-line managers should coach first-line managers on weekly accountability, how to set clear expectations that cascade through the organization, and why most companies misalign their manager responsibilities. If your managers don't have clarity on how to execute week to week, your reps won't eith...

Most companies spend September and October planning for 2027, but they skip the part that actually matters: figuring out how their teams will execute on it. That's why we're revisiting this episode with Dr. Chuck Bamford, who walks through how to align strategy from the boardroom all the way down to compensation plans, daily activities, and the conversations your reps have with customers. He covers what separates strategy that gets executed from strategy that sits on a shelf, and why most execution failures have nothing to do with the strategy itself. If you're mapping out your revenue goals for next...

Winning complex deals requires more than executive sponsorship. The strongest business cases are built by connecting value across the organization. Daniel Simon shares how he worked with stakeholders across product, engineering, finance, HR, and legal teams to uncover specific use cases, quantify time savings, and build an ROI story that resonated from end users to the executive team. The result was a business case that transformed AI from a technology investment into a measurable business outcome.

Daniel Simon is an Enterprise Account Executive at Glean, where he helps large enterprises deploy AI solutions that improve knowledge discovery...

CROs who chase pipeline numbers miss what really matters. Sam Costello's path from sub-$1M to $100M at Harness taught him to stop managing revenue and start building the machine that produces it, which means recruiting elite, coachable talent, running a champion-first sales process with discipline, and building a culture of radical candor where MEDDPIC reviews are hunts, not compliance exercises. If you're spending more time managing numbers than building people and process, this conversation reveals where that shift starts – and what it costs to miss it.

Sam Costello is CRO at Harness, where he's spent 7.5 years sc...

AI adoption has changed the standard for go-to-market execution. Seong Park, SVP of Customer Support & Services at Cursor, explains why the old model of selling certainty is giving way to curiosity, experimentation, and workflow discovery. He breaks down why the real work starts after signature, why pilots only matter if they lead to business-critical adoption, and how revenue leaders can guide customers from AI exploration to measurable impact.

Seong Park is the Senior Vice President of Customer Support and Services at Cursor. His background spans pre-sales, customer success, and go-to-market leadership across companies including MongoDB, ThoughtSpot, and...

Michelle Bove didn't start in enterprise software – she started as a soccer referee in seventh grade, hustling for an extra $10 per game, then moved into door-to-door sales at a three-person startup where she learned rejection quickly and loved it even more. That hunger never left. Today, as an AVP of East Sales at Wiz, she's built her career at some of the sharpest sales cultures in software history (PTC, AppDynamics, Zscaler), closed deals nobody else could get into, and turned around entire teams by replacing broken managers instead of blaming reps. In this conversation, she breaks down the real me...

High-performing teams create the conditions for talent to succeed. In this Revenue Builders segment, Lindsay Shookus shares lessons from Saturday Night Live on cultural fit, team buy-in, trust, and performance under pressure. Drawing from examples of SNL talent who found success in different environments, Lindsay explains why fit often determines whether strong people can thrive inside a specific team rhythm. She also shares how leaders can create safety for risk-taking, give teams ownership in new hires, and reduce the pressure on individuals by helping them trust the room around them.

Lindsay Shookus spent 20 years at Saturday Night...

Most sales conversations still lean on product specs, and most leadership still gets reduced to quota math, until the market gets hard and both approaches break down. Rob Potter, CEO of Oomnitza, joins John Kaplan and John McMahon to argue that revenue and retention run on the same fuel: story, evidence, and belief rather than pressure. Shaped by three decades under RSA and EMC leaders like Art Coviello and Mark Thurman, Potter explains why technical credibility alone creates gaps in a sales motion, how staged delegation and reverse-timeline planning scale a team without inflating cost, and why transformative leaders...

Enterprise sellers often lose deal quality by moving too quickly from customer pain to product answers. In this Revenue Builders minisode, Stuart Gwynn of MongoDB explains why the best sellers slow down in discovery, hold the line with the customer, and use disciplined qualification to determine whether a problem is real, urgent, and worth solving. Stuart shares how pipeline creates the courage to qualify out, why team preparation matters before strategic customer conversations, and how trust is built when sellers demonstrate that they understand the customer’s business before prescribing a solution.

Stuart Gwynn is an enterprise sa...

Senior leaders are often judged in moments they could not plan for. Mark Thurmond’s path from sales rep to co-CEO of Tenable was built through consistent execution, difficult operating assignments, and crises that demanded calm before certainty. He explains what the RSA breach taught him about transparency and customer trust, how he and Steve Vintz kept Tenable moving after the death of CEO Amit Yoran, and why the strongest leaders build followership before they need it. The conversation also covers choosing learning over title, using AI to raise seller productivity, and leading a product-to-platform shift as a company-wide op...

In this clip, Alex Bilmes, CEO of Endgame, joins Revenue Builders to share what his team learned from analyzing more than 30,000 real AI workflows across go-to-market teams. The data shows AI gaining traction in account intelligence, conversation readiness, deal acceleration, pipeline inspection, and team enablement. But the larger lesson is that the strongest teams are not just using AI to generate decks, briefs, or follow-ups faster. They are using it to create shared understanding across reps, managers, executives, RevOps, and cross-functional teams. For revenue leaders, the opportunity is not simply more automation. It is connecting the organization around the...

AI partnerships are no longer won by managing a channel or securing a marketplace listing. Leaders must understand how countries, power, cooling, chip fabrication, hyperscalers, model providers, software companies, and enterprise risk fit together before they can build an effective partner strategy. Returning to Revenue Builders, Alan Chhabra explains how Cerebras navigated the technical and political realities of working with AWS, why successful partner leaders need more than relationships, and how sovereignty is changing infrastructure, model selection, and cloud decisions. He also examines why software companies are moving aggressively on AI while traditional enterprises remain more cautious.

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High-pressure sales moments test a leader’s ability to stay composed, present, and clear when the outcome matters. In this minisode, Dr. Michael Gervais explains how elite performers manage activation before critical moments, from major buyer meetings to executive presentations. He breaks down the difference between useful nerves and disruptive anxiety, then outlines the mental skills that help leaders regulate pressure: awareness, breathing, and self-talk. For revenue leaders, this conversation offers a practical lens on preparing the mind before the stakes arrive.

Dr. Michael Gervais is a performance psychologist, the founder of Finding Mastery, host of the Fi...

Pressure does not create a response. It exposes the response that has already been trained. Former professional hockey coach and mental strength coach Greg Poss returns to explain how leaders can recognize fear-driven reactions, return to a more deliberate state, and build resilience before the stakes rise. Greg, John McMahon, and John Kaplan examine why external achievement delivers only temporary satisfaction, how a leader’s emotional state influences the performance of the team, and why productive discomfort must be paired with a clear path forward. They also discuss practical tools including breathing, visualization, self-awareness, and Greg’s 21-day process for...

Late-stage deals can appear secure once the buyer has accepted the product and the business case, but that is often when the risk feels most personal. In today’s segment, Randy Riemersma explains why deals inside the final 10 yards are won or lost on buyer confidence and how elite sellers remove doubt through executive alignment, credible proof points, consistent communication with the champion, and a clear business-level point of view. The conversation gives revenue leaders a sharper way to evaluate late-stage deal risk and reinforces why belief, preparation, and execution matter when the buyer is preparing to make a hi...

Sales organizations stall when knowledge stays trapped in the heads of a few experienced people. In this Revenue Builders replay, Frederik Maris explains how leaders turn field experience into repeatable execution through sharper qualification, stronger frontline management, and deliberate coaching. He shares how conscious competence helps managers teach what top performers do instinctively, why early wins matter for new reps, and where leaders must take accountability when talent fails to develop. The conversation gives CROs a practical view of the systems, behaviors, and management discipline required to build a team that can scale.

Frederik Maris is the...

Automation has increased sales activity while reducing effectiveness, as AI-driven outreach floods the market and drives conversion rates down. In this segment, Greg Casale explains why outbound phone calling remains a critical channel for pipeline generation, especially in complex B2B environments where live conversations create immediate learning and engagement. He outlines the discipline required to make phone work, from hiring and training to technology and compliance, and why this channel continues to perform when easier options break down. The discussion highlights a clear operational reality for sales leaders: teams that invest early in outbound phones build a durable...

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 "patriots" from "mercenaries" in the hiring process, and the operating principles that produce durable sales organizations.

Chad Peets is the Managing Partner of RPT Partners and has spent more than 25 years helping software companies...

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 competition, product strategy, and go-to-market execution. He also explains how Cursor’s multi-model approach creates a unique advantage in a fast-moving market, and why aligning that innovation with focused sales execution is critical to winning.

Brian McCa...

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 explains why elite sellers slow down early, uncover real business pain, connect operational problems to strategic outcomes, and manage the emotional side of buying when the decision starts to feel personal.

Randy...

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 who get hands-on with AI will operate at a different level, while those who don’t risk falling behind faster than they expect.

Alex Varel is EVP of Worldwide Sales at Ce...

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 conversation explores the role of RevOps as a strategic advisor to leadership, the importance of building a strong middle class of sellers, hiring for adaptability and coachability, and creating cultures where problems surface early. Jason also shares how open-source adoption can be transformed into enterprise-wide business...

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 emerges through those early conversations. For leaders, this is a reminder that sales is not something you hand off. It’s how...

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 relying on product excitement alone.

Daniel Simon is an Enterprise Account Executive at Glean, where he works with large enterprises on AI adoption, knowledge...

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 any one of these creates pipeline risk, and how leaders can avoid over-rotating into segments th...

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 into customer workflows, what finance scrutiny means for consumption models, and why the fundamentals of pain, champions, outcomes, and evidence still matter in a...

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 guidance on how to achieve forgiveness through self-inventory, humility, and learning from challenging moments rather than dwelling on negative feelings.

Doug Holladay is an author, educator, and leadership advisor...

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 process that allows strong personalities to perform together. She also shares leadership lessons from Lorne Michaels, the importance of adaptability and...

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 product presentations should only happen when the value proposition is clear, and how leaders can motivate reps by speaking directly to...

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 champion will actually sell internally, and why large deals require multiple stakeholders, rigorous qualification, and a team operating around a shared account vision. He...

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, and structured engagement, not just hiring more talent. For leaders trying to build repeatability in complex sales, this is a clear look at what it takes.

Sahir Azam...

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 intelligence layer, how to prevent inconsistent messaging at scale, how RevOps must evolve, where AI can accelerate ramp and account coverage, and why human judgment becomes...

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 professor, director of MIT’s Statistics and Data Science Center, and co-founder and CEO of Ik...

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 mental skills like awareness, breathing, self-talk, imagery, and honest team dynamics help people operate with more clarity under pressure. The conversation brings pe...

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 just to increase productivity, but to create space to think, coach, and lead more effectively. For CROs and frontline managers, this raises...