Episode Library

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.

Veteran enablement leader Tom Kiernan and I debate the forbidden "T-Word"—Training. Tom argues that effective enablement isn't a one-time event but a continuous process akin to the "Toyota Way," and challenges the industry's "Practice Deficit" where sales reps, unlike professional athletes, often treat live calls as their practice fields. We dive into the neuroscience of the Reticular Activating System (RAS) to explain how buyers filter out noise, and why removing "Commission Breath" is the only way to hack their attention and build genuine trust.

Episode Summary
Are you part of the 82% of leaders who feel like "Accidental Managers"? In this episode of Thoughts on Selling, Lee Levitt talks with Ben Perreau, a former music journalist turned leadership expert and founder of Parafoil.

We discuss the most dangerous leap in any career: the transition from Individual Contributor (IC) to Team Leader. Ben explains why companies set new managers up to fail by promoting them for technical skills but ignoring the emotional intelligence required to ...

Episode Summary
Is the "growth at all costs" era over? In this episode of Thoughts on Selling, Lee Levitt sits down with Amos Bar-Joseph, a third-time entrepreneur joining from Tel Aviv, to dismantle the broken "Unicorn Playbook."

Amos describes himself as an "Anti-Capitalist Capitalist," rejecting the traditional VC model of raising massive rounds to hire bodies. Instead, he is building Swann, an Autonomous Business designed to scale with Artificial Intelligence, not headcount. We explore why ...

In this episode of Thoughts on Selling, Lee Levitt sits down with ETA leader Garth Fasano to discuss the massive shift from traditional inside sales to "Agentic AI"—autonomous agents that think, adapt, and sell without fatigue. Garth explains why small businesses are adopting this technology faster than enterprises to solve the "consistency" problem, ensuring every prospect gets a "fully caffeinated" interaction even after 175 calls. We also explore the future of "Bot-to-Bot" commerce, where AI buyers negotiate with AI sellers, and how this shifts the sales function from simple execution to strategic business visibility.

Episode Summary
What do selling gum in the 5th grade and playing defense in hockey have in common with high-stakes Enterprise Sales? According to Nina Iannuzzi, absolutely everything.


In this episode of Thoughts on Selling, Lee Levitt sits down with Nina, a sophomore at the Isenberg School of Management (UMass Amherst) and a top-tier finalist at the recent National Intercollegiate Sales Competition (NISC).


If you think the next generation of sales talent is "soft," you haven’t met Nina. We...