Episode Library

Your car goes where your eyes go." That's a high-performance driving lesson — and it's the perfect metaphor for what's gone wrong in B2B sales. We've been staring at the wrong thing.

I'm Lee Levitt — sales coach, podcast host, and author of The Second Meeting and Together We Win, both due out later this year. Today I'm sitting down with Tom Pisello, known across the industry as The ROI Guy. Tom's been a value-selling pioneer for over 30 years — from his days as the Godfather of TCO at Gartner to founding GeniusDrive.

Buyer confidence is at an all-time low. More information, bigger committees, better tools — and yet two-thirds of buyers regret their decisions shortly after the ink dries. Why?

Here's what to listen for: Aristotle's three buy buttons — pathos, logos, and ethos — and why trust now accounts for 50% of the decision. The shift from fear of missing out to fear of messing up. And why more information doesn't create more confidence.

If you've ever had your best ROI …

Chris Carter — technologist, keynote speaker, and SAP ecosystem veteran — joins Lee to unpack what it actually means to use AI well in enterprise selling. From using Gemini to simulate discovery conversations to the Peloton analogy that woke up a room of Oracle salespeople, this episode is about preparation, strategy, and making your own rules. If you're firing off AI-generated emails and wondering why nobody's responding, this one's for you.

Gina Smith didn't plan to spend 27 years in sales. She planned to stay in HR — until a sales manager walked into her office and asked if she knew anyone who could fill an open role. She interviewed. She won. And what followed was a career that taught her everything she needed to know about trust, listening, and what actually moves buyers in complex environments.

In this conversation, Gina and Lee explore the gap between what people believe salespeople need to be and what the best salespeople actually are. They cover the shift in hospital buying dynamics, why honesty is a competitive advantage, and why no amount of process documentation will close the gap when the real variable is who you show up as. A sharp, grounded conversation for anyone selling in environments where the relationship has to come before the recommendation.

Danny Bobrow—communication coach, mountaineer, and creator of the Persuasion Blueprint—joins me for a conversation about the science and art of persuasion. Danny spent 36 years in marketing before discovering that getting the phone to ring was only half the problem—how calls were handled determined success or failure.

That led him to develop a framework built on three C's: Caring, Connection, and Collaboration. We dig into the brain science of resistance (amygdala, limbic system, prefrontal cortex), Mehrabian's research showing words account for only 7% of effective communication, and the counterintuitive lesson from a health club saleswoman who outsold everyone by letting prospects stay in control.

Danny's mountaineering background surfaces throughout—the psychological fatigue barrier, "patiently persistent and respectfully resilient," and the Sherpa model for coaching. If you've ever wondered why your best facts-based pitch falls flat, this conversation will show you what's ac…

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 toy—became the foundation of Sendoso, now the largest direct mail and gifting platform in the world. We cover the psychology of reciprocity, why the open rate of a FedEx box is 100%, and why dimensional mail is the channel that never stopped delivering.

The Kansas City ribs story is one you won't forget: a prospect broke a rib skiing, so the Sendoso team sent a rack of BBQ ribs to his office. He shared the story with his whole company, and they got the deal.
Kris's motto—"people buy from pe…

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…