Revenue Builders

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...

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 saturated the market and reduced conversion rates, and where AI fits as a tool to strengthen preparation and execution without replacing human interaction. 

Greg Casale is the Founder and CEO of R...

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-negotiable for sellers operating at the highest level.

Jane Thompson is a sales leader at BigPanda with deep experience selling into complex, multi-division enterprise accounts and building high-impact strategic sales motions.

Connect...

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 how AI is reshaping productivity, why ICPs must evolve weekly, and how elite sellers distinguish themselves by orchestrating value across increasingly complex buying groups.<...

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 more effective sellers, this is a perspective worth revisiting.

Chris Vik is VP EMEA at Samsara and a...

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 machine that keeps pace with innovation while deepening customer trust.

Brian McCarthy is President of Global Revenue and Field Operations...

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 conditions for authentic customer conversations.

John Rowell is the Co-Founder of Pinned Golf and a former enterprise sales leader with experience at EMC and Lacework. He...

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 stall. He introduces frameworks like the “problem with the problem” and the “murder board,” while reinforcing a consistent theme: sales is not a downstre...

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.

John Donnelly is a seasoned enterprise sales leader and CRO with a track record of scaling high-growth organizations through IPOs and ac...

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 operating system rooted in use cases, lifetime value, and market health. The conversation challenges traditional go-to-market structures, highlights the risks of misaligned incentives...

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 signals actually look like, and how sales teams should adapt their timing, messaging, and motion accordingly.

Dan Fougere is...

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 is reshaping both software and the sales function itself. The conversation also challenges common assumptions around SaaS models, tooling, and where value will accrue as AI infrastructure matures.<...

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 make better decisions before problems show up in the number. If you’re a CRO, founder, or sale...

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 drive curiosity, coaching, and clarity in how their teams actually sell and hire.

Marcy Stoudt is Founder of Revel Companies, where...

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, how genuine connection creates trust, and why discipline only works when it’s grounded in relationship.

Coach John Mosley Jr...

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 connect pipeline generation to partners, community, field marketing, and recruiting to create durable growth. This conversation reframes pipeline as a leadership resp...

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 discusses how this evolved understanding of persona dynamics becomes essential when transitioning from being an individual seller to leading and scaling a sales team.

Eric...

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 investor perspective. The conversation explores how CRO-CEO alignment shapes company performance, why sales efficiency has become a defining metric in private...

In today's minisode, AI pioneer and enterprise sales leader Amanda Kahlow shares why intent data as we know it is dying – and what replaces it. Amanda is the founder and CEO of 1mind. In this segment, she discusses how SI  “superhumans” can operate inside live deals with access to every document and data point, and why the future of go-to-market may move toward agent-to-agent negotiation… with humans stepping in only for the final mile. If you're a CRO rethinking your funnel, a sales leader questioning the future of the SDR role, or an operator trying to understand how AI fits into...

Amanda Kahlow joins Revenue Builders to unpack what happens when AI stops assisting go-to-market teams and starts replacing entire functions. Drawing on her experience founding SixthSense and now leading 1mind, she explains how technology originally built for Alzheimer’s caregivers evolved into AI “superhumans” capable of running demos, qualifying buyers, building business cases, and onboarding customers. The conversation gets real about some of the uncomfortable questions facing sales today: what happens to SDRs, how the AE role changes, why traditional handoffs between Sales, Marketing, and Customer Success break down, and what “the final mile” of human selling really looks like. For...

In this minisode, Cedric Pech, President of Field Operations at MongoDB and former CRO, shares a formative leadership moment from early in his career at PTC that shaped how he thinks about building revenue organizations. He tells the story of a manager who invested in him personally before he had proven himself professionally. It is a lesson in what real leadership looks like under pressure. For CROs and frontline leaders alike, this clip is a reminder that culture is built in moments like these, not in mission statements.

Hosted by five-time CRO John McMahon and Force...

Scaling from regional VP to global CRO is not a promotion. It is a shift from managing execution to defining meaning at scale. In this replay conversation, Cedric Pech reflects on leading a 2,000-person global sales organization at MongoDB, integrating complex routes to market, and building culture that withstands market volatility. He breaks down the difference between compensation-driven leadership and purpose-driven leadership, why execution alone creates burnout, and how resilient organizations are built long before downturns arrive. For CROs and revenue leaders navigating scale, volatility, or retention pressure, this episode offers a grounded perspective on building durable teams without...