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.
Jul 2
1 hr 1 min
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.
Jun 28
11 min
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.
Jun 25
1 hr 7 min
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.
Jun 21
14 min
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.
Jun 18
1 hr 1 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.
Jun 14
11 min
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.
Jun 11
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.
Jun 7
16 min
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.
Jun 4
59 min
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.
May 31
6 min
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