Episode Library

Juan García—co-founder of Tuio, an AI-native insurer based in Spain—joins me to talk about what happens when you rethink an industry from first principles. Juan started in engineering at Cisco, moved through strategy consulting, and then built Orange Insurance—where he saw just how broken the insurance industry really was.
The 25-55 customer segment is digitally native. They buy groceries online, manage finances on their phones, and don't want to call anyone. But legacy insurers weren't built for them—and worse, this segment was unprofitable because they're too informed. They use price comparison sites. They read Trustpilot. They know what they're buying.
So Juan and his co-founders built Tuio: a self-service, data-driven platform where customers actually buy insurance themselves. They went against the industry mantra—"insurance is not bought, it's sold"—and proved it could work.
The AI applications are fascinating. They can see which device you're browsing from and adjust risk pri…

Joe Terry—former CEO of Corporate Visions and co-author of the USA Today bestseller Surrender to Lead—joins me for a conversation about what actually drives results.

We dig into the action trap (why hitting every activity metric still misses the number), the results pyramid (experiences → beliefs → actions → results), and the mindset shift that changes everything: showing up to give, not to get.

Joe shares the SHIFT framework for getting out of your own way, the four questions that make buyers stop and pay attention, and why 12 executives in the same room will give you 12 different answers to "What are our top three objectives?"

This one's for anyone tired of inspecting pipeline and ready to start coaching belief.

Frankie Kemp brings a unique blend of acting, behavioral science, and communication coaching to a conversation about what actually makes someone persuasive. We explore Aristotle's three pillars—logos (data), ethos (credibility), and pathos (emotion)—and why most technical specialists lean too hard on just one. Frankie shares how she's helped close multimillion-pound deals with small nonverbal adjustments, why improv training is showing up in pharma and finance, and how to identify someone's learning style just by listening to the words they choose. The big takeaway: communication isn't about being smooth—it's about being adaptable.

Enterprise sales is under pressure to adopt AI sales strategies. But...in enterprise sales, the mindset of the sales rep still dictates success or failure.

James Stephan-Usypchuk brings 15 years of AI development experience and a psychology degree to a conversation about what machines can and can't replace in sales. We explore why trust still requires a human face, how predictive algorithms should be used as filters rather than closers, and why likability remains the ultimate competitive advantage in an AI-saturated market. James shares real examples from his work with private equity firms, including how his team uses AI to identify acquisition targets—but always injects the human element when it's time to have a real conversation.

Sales and marketing alignment isn't a nice-to-have — it's the engine that drives predictable revenue. In this episode of the Thoughts on Selling podcast, I talk with Javier Lozano Jr., a fractional CMO and CRO who helps founder-led tech companies build the infrastructure where sales and marketing actually work together. Javier brings a rare perspective: he's lived on both sides of the revenue equation, and he's seen firsthand what happens when these teams are aligned on revenue goals versus when they're tossing leads over the fence and pointing fingers.

We get into some meaty territory — why customer success is really a marketing function (because those customer stories become your best sales enablement), how AI is already transforming the way smart teams analyze sales conversations and sharpen their messaging, and why the feedback loop between sales, marketing, and operations is a closed system that breaks when any piece gets out of sync. Javier shares a metric he calls HIRO pipel…

In this episode of Thoughts on Selling, Lee Levitt sits down with Drew Sechrist, CEO of Connect the Dots and an early Salesforce employee, to discuss the evolution of sales from the "No Software" era to the age of AI. Drew shares insights from his time working alongside Marc Benioff, emphasizing the critical role of "osmosis" in learning sales skills—a benefit he fears is being lost in today's remote-first work environment. He argues that while technology has made many aspects of sales easier, the loss of in-person mentorship and hallway conversations has made the profession harder for newcomers to master.

The conversation pivots to the future of selling in an AI-dominated world, where Drew asserts that "trust capital" is the only durable moat for sellers. As AI automates routine tasks, the human ability to build deep, high-stakes relationships becomes more valuable than ever. Drew explains how his company, Connect the Dots, is helping sellers leverage their "relationship capital" …

Most companies pour their resources into new business while ignoring the account management strategy that actually drives profit. In this episode, Alex Raymond — founder of AMplify and author of The Growth Department — shares why 73% of revenue and nearly all profit come from existing customers, and what a winning account management strategy looks like in practice. His Keep, Grow, No Surprises framework gives sales leaders, CSMs, and CROs a clear path to retain more customers, drive expansion revenue, and stop treating post-sales like the JV team.

Carole Mahoney, author of Buyer First, shares her mission to change the negative perception of sales. We discuss the power of "cognitive behavioral" sales training, why improv is a crucial skill for modern sellers, and how a manager's mindset can statistically predict a team's success or failure.

In this episode of Thoughts on Selling, Lee Levitt sits down with Amos Balongo—a leadership expert who is in the business of "manufacturing leaders" to be exceptional communicators. We dig into the critical gap where strategy fails: when leaders rely on "Positional Authority" ("I told you to do this") rather than "Influential Leadership" that invites collaboration. Amos breaks down his framework for moving teams from simple motivation (an "outside job") to genuine inspiration (an "inside job") and finally to transformation , explaining why simplicity mobilizes teams better than complexity and how applying "Situational Leadership" prevents communication breakdowns.

Pete Smith, founder of SpotLogic and veteran sales leader, discusses why enterprise sales reps are drowning in tools and still starving for insight. We discuss the "Cognitive Load" crisis in modern selling.

We explore why 84% of enterprise deals stall after the first meeting and how Sales Enablement leaders can help reps stop "winging it" and start winning. From his days at NCR’s legendary "Sugar Camp" to building deal intelligence software, Pete reveals how to earn the status of a "Trusted Insider" rather than just another vendor.