Humility & The Art of Letting Go with Doug Holladay

The Real Sale Starts After Signature | Proving Value in AI and Consumption Models with Seong Park

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 market moving at unusual speed. 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 now Cursor. Connect with Seong: * LinkedIn [https://www.linkedin.com/in/seong17/] Key takeaways from this episode:  * 00:00 – Seong Park’s perspective on how pre-sales, open source SaaS, and customer success shaped his view of enterprise go-to-market. * 02:26 – Why consumption models force revenue teams to re-earn the customer’s business through usage and realized value. * 08:00 – The value realization test every revenue leader should care about: what happens if the solution gets unplugged. * 11:04 – Why workflow depth quietly becomes a moat in enterprise accounts. * 18:04 – Why the real selling often starts after the customer signs. * 23:50 – A look inside where Cursor is finding technical go-to-market talent, and what it takes to build that talent into customer-facing operators. * 34:38 – Why finance scrutiny quietly changes the standard of proof for AI investments. * 52:00 – The three things post-sale teams need to understand before value delivery can begin. Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.    This show is brought to you by Force Management [https://www.forcemanagement.com/]. We help companies improve sales performance, executing their growth strategy at the point of sale.    Connect with Us:  * LinkedIn [https://www.linkedin.com/company/revenue-builders-podcast/] * YouTube [https://www.youtube.com/@Forcemanagement] * Force Management [https://www.forcemanagement.com/]

Humility & The Art of Letting Go with Doug Holladay

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 known for helping leaders examine the internal patterns that shape culture, decision-making, and long-term success. He is the author of Rethinking Success and a frequent contributor to conversations on leadership, humility, and organizational health. Resources mentioned: * Rethinking Success by Doug Holladay [https://www.amazon.com/Rethinking-Success-Essential-Practices-Finding/dp/0062897888] * The Wounded Healer by Henri Nouwen [https://www.amazon.com/Wounded-Healer-Ministry-Contemporary-Society/dp/0385148038] * What Happened to You? by Bruce Perry and Oprah Winfrey [https://www.amazon.com/What-Happened-You-Understanding-Resilience/dp/1250223180] Listen to the full episode: * Forgiveness as a Leadership Advantage with Doug Holladay, Author of Rethinking Success [https://podcasts.apple.com/us/podcast/forgiveness-as-a-leadership-advantage-with-doug/id1610203369?i=1000744268963] Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.    This show is brought to you by Force Management [https://www.forcemanagement.com/]. We help companies improve sales performance, executing their growth strategy at the point of sale.    Connect with Us:  * LinkedIn [https://www.linkedin.com/company/revenue-builders-podcast/] * YouTube [https://www.youtube.com/@Forcemanagement] * Force Management [https://www.forcemanagement.com/]

How Saturday Night Live Builds Teams That Perform Under Pressure with Lindsay Shookus

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 coachability, and why authentic connection gives teams the confidence to take risks when the stakes are highest. Lindsay Shookus spent 20 years at Saturday Night Live, including 10 years as a producer, where she led talent booking, worked with celebrity hosts and musical guests, and helped scout and recruit cast members. She is a four-time Emmy Award winner, a former producer on 30 Rock, and the co-founder of Women Work Hard, a community supporting female entrepreneurs and leaders. Connect with Lindsay: * Website [https://www.lindsayshookus.com/] Resources mentioned: * Women Work Hard on IG [https://www.instagram.com/womenworkfinghard/?hl=en] * Women Work Hard Website [https://wwfh.community/] * Rethinking Success by J. Douglas Holladay [https://www.amazon.com/Rethinking-Success-Essential-Practices-Finding/dp/0062897888] Key takeaways from this episode: * 00:00 - Introduction * 06:25 - What it really takes to build trust quickly when high-performing people have only days to align. * 14:22 - Why many leaders misread talent when they rely on credentials instead of team fit, coachability, and social awareness. * 07:55 - A look inside how high-pressure decisions get made when timing is tight and every stakeholder has a point of view. * 11:46 - Why hiring people who can take your job quietly raises the standard for the entire organization. * 37:35 - What leaders often overlook about coachability once someone has already reached the top of their field. * 43:49 - Lindsay Shookus’ perspective on why vulnerability creates stronger leadership connections than polished perfection. * 51:36 - Why strategic absence can make a leader’s presence more valuable. Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.    This show is brought to you by Force Management [https://www.forcemanagement.com/]. We help companies improve sales performance, executing their growth strategy at the point of sale.    Connect with Us:  * LinkedIn [https://www.linkedin.com/company/revenue-builders-podcast/] * YouTube [https://www.youtube.com/@Forcemanagement] * Force Management [https://www.forcemanagement.com/]

John McMahon on Building a Better SKO

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 their daily challenges, career aspirations, and earning potential. John McMahon is a five-time CRO who has led revenue organizations at PTC, GeoTel, Ariba, BladeLogic, and BMC. He is the author of The Qualified Sales Leader and co-host of Revenue Builders, where he brings operator-level perspective on building and scaling enterprise sales teams.  Connect with John: * LinkedIn [https://www.linkedin.com/in/johnmcmahon1/] * Book [https://www.amazon.com/dp/0578895064] Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.    This show is brought to you by Force Management [https://www.forcemanagement.com/]. We help companies improve sales performance, executing their growth strategy at the point of sale.    Connect with Us:  * LinkedIn [https://www.linkedin.com/company/revenue-builders-podcast/] * YouTube [https://www.youtube.com/@Forcemanagement] * Force Management [https://www.forcemanagement.com/]

The Discipline Behind Nine-Figure Deals with Stuart Gwynn

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 also shares how elite individual contributors lead without formal management titles, where AI is already changing buyer expectations, and why process only works when it is paired with judgment. Stuart Gwynn is an enterprise sales leader at MongoDB who has exceeded goal every year since joining the company in 2019. Before MongoDB, he spent seven years at Pure Storage, rising from SDR to named account rep and finishing as one of the company’s top performers before moving into strategic enterprise selling. Connect with Stuart: * LinkedIn [https://www.linkedin.com/in/stuartgwynn/] Episodes mentioned: * The Discipline Behind Scaling from PLG to Enterprise with Sahir Azam [https://podcasts.apple.com/us/podcast/the-discipline-behind-scaling-from-plg-to-enterprise/id1610203369?i=1000758846474] * Why Sales Execution Wins in an AI-First World with Brian McCarthy, President of Global Revenue and Field Operations at Cursor [https://podcasts.apple.com/us/podcast/why-sales-execution-wins-in-an-ai-first-world-with/id1610203369?i=1000763245657] Key takeaways from this episode: * 00:00 – What it really takes to combine a rigorous value framework with the human judgment required to scale enterprise selling. * 02:42 – Why discovery becomes the moment where real pain, executive relevance, and budget-worthy outcomes either surface or disappear. * 07:59 – What leaders often overlook about the trust required before customers will quantify the true cost of a problem. * 11:28 – Why champion identification quietly determines whether a deal has internal momentum or only surface-level support. * 21:35 – The mistake many sellers make when pipeline pressure pushes them toward activity instead of disciplined qualification. * 18:50 – A look inside the preparation habits that help enterprise teams align before high-stakes customer conversations. * 56:25 – Why many leaders get top-talent management wrong by applying the same operating rhythm to every rep. Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.    This show is brought to you by Force Management [https://www.forcemanagement.com/]. We help companies improve sales performance, executing their growth strategy at the point of sale.    Connect with Us:  * LinkedIn [https://www.linkedin.com/company/revenue-builders-podcast/] * YouTube [https://www.youtube.com/@Forcemanagement] * Force Management [https://www.forcemanagement.com/]