Categories: Podcasts
Buyers expect sellers who understand their business, and teams are still working out where AI fits in their sales process. October's lineup covers deal architecture, mental performance, risk-taking, and the alignment behind AI adoption, with guests who have built and coached revenue teams across the buying journey. From discovery discipline to the inner game, each episode brings frameworks and firsthand experience for leaders planning a stronger 2027.
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October Featured Episodes:
Why Deals Don't Close: Anne Gary's Framework for Discovery, Champions & Economic Buyers
Duration: 1 hr 13 min
Topic:
Most deals die quietly in discovery, champion development, or economic buyer misalignment. But what actually separates consistent closers from perpetual stallers? In this replay, Anne Gary sits down with John McMahon and John Kaplan to reveal the blind spots in your sales process – and the coaching framework your leadership team needs before you finalize your 2027 plan. From preparation rituals to multi-threading strategy to navigating proof of value, Anne walks through the entire deal architecture that most teams get wrong.
Anne Gary is Managing Director at Force Management and a member of the founding team of the MEDDPICC qualification methodology. She's spent 25+ years coaching thousands of sales professionals and leaders on building repeatable, predictable deal strategies across Fortune 500 companies and high-growth startups.
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Why Risk Takers Build the Most with Doug Holladay, Author of Rethinking Success
Duration: 1 hr 5 min
Topic:
Many leaders spend their careers chasing a scoreboard someone else set. It works until the how stops working, and nobody ever trained them on the why. This conversation picks up our Rethinking Success series dissecting the definition of success and failure for yourself while inviting real risk into your life. John McMahon connects a study of high school valedictorians to the sellers who win complex enterprise deals, and John Kaplan opens up about how fear of failure shaped his own path. Doug Holladay explains why the people who embrace setbacks build the most, and how leaders can start examining their own story before a crisis forces it.
Doug Holladay is the founder & CEO of PathNorth, a Georgetown MBA professor, a former Goldman Sachs senior officer and White House Special Ambassador, and the author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life.
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The Inner Game Most Sales Leaders Never Coach with Collin Henderson
Duration: 1 hr 11 min
Topic:
Most sales leaders coach the outer game: pipeline, routing plans, pricing, KPIs. That’s maybe 15 percent of performance. The rest sits under the surface in self-doubt, fear of other people’s opinions, and the stories reps tell themselves about who they are. Collin Henderson was a two-sport Division I athlete who developed a stutter at 11 and once pre-recorded his answers to a pharma sales evaluation, so he knows what happens when that layer goes untrained. In this one, he breaks down why talent plus skill minus internal interference equals execution, and walks through the three-step influence system from his book The Oz Method.
Collin Henderson is a mental performance coach, keynote speaker, and founder of Master Your Mindset, LLC, who has trained teams at Nike, Amazon, Microsoft, and Salesforce, and shares how to connect with him and get his new book, The Oz Method, at the end of the episode.
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Why Enterprise AI Agents Struggle to Reach Production with Open Source Pioneer Ben Sabrin
Duration: 1 hr 4 min
Topic:
Enterprises have poured money into AI, and most of it is still doing research. The return comes when agents start taking action inside real systems, and that’s where most companies get stuck. If no one can say who authorized an agent to take a specific action, across specific systems, at a specific time, that agent never leaves the pilot. Arcade, fresh off a $60 million raise, was built to answer that question. Ben Sabrin, an open source pioneer who built early sales teams at JBoss and MongoDB, leads its go-to-market. He explains what it takes to sell a category this new, why repeatability has to come before scale, and how he runs his own sales team on AI.
Ben Sabrin is the GTM Lead at Arcade.dev and a former CRO at ngrok and ScaleFT who has spent more than 20 years building early sales teams at companies including JBoss, MongoDB, and Okta.
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Why AI Is Making Your Reps Sound Like Everyone Else with Matt Fermino
Duration: 1 hr 4 min
Topic:
Sales teams have never had more research at their fingertips, and buyers still say reps don’t understand their business. The prep docs look great right up until someone asks how the customer actually makes money. Matt Fermino calls it Seller Deficit Disorder. He joins John McMahon and John Kaplan to break down how AI turns information into a crutch, how his leaders use call recordings to coach tone and likability, and why coachability matters more in hiring than where a candidate is today.
Matt Fermino is the Chief Revenue Officer at Fable Security and previously held senior sales leadership roles at Astronomer, Starburst, and Cybereason.
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Never Miss an Episode
We publish new episodes every week. Download, listen and share them with your teams. If there's a topic you want us to cover, email us. You can subscribe to our podcast on all the major streaming platforms.
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