Kris Rudeegraap—co-founder and co-CEO of Sendoso—joins me to talk about what happens when email stops working and you have to find another edge. Kris was a top seller who got 90% response rates in the early 2010s using mail merge. Then email sequencing tools flooded the market and response rates tanked. So he started sending handwritten notes, dog toys, and swag from the marketing closet—and booking more meetings than anyone else.That curiosity—hearing a dog bark on a call and sending a dog…
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 …
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 b…
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 lea…
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 ta…
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 whe…
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, …
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 r…
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") …