Thoughts on Selling - Value Selling, Sales Leadership, Sales Enablement Insights

Buyer confidence is at an all-time low — and more data isn't fixing it. In this episode, Lee sits down with Tom Pisello (The ROI Guy), value-selling pioneer and founder of GeniusDrive, to unpack why B2B deals stall even when the numbers are solid. Tom and Lee explore Aristotle's three buy buttons, the shift from FOMO to fear of messing up, why trust now drives 50% of the purchase decision,...

Chris Carter has been in the SAP ecosystem for decades — and he's watched AI go from expert systems on a Commodore VIC-20 to a tool that's genuinely changing how enterprise companies forecast, plan, and sell. He's not impressed by the hype. He's impressed by the people who actually use it well. In this episode, Chris and Lee cover what separates the sellers who are winning right no...

Gina Smith spent 27 years selling medical devices into hospital operating rooms — and she got there entirely by accident. No role models. No sales background. A career in HR she was tired of. One conversation with a sales manager who couldn't fill a role. And a "mercy interview" she then went out and won. In this episode, Gina and Lee dig into what actually drives sales performance i...

Danny Bobrow has spent 36 years in marketing and communications. He discovered a hard truth about sales effectiveness: getting the phone to ring is only half the battle. What happens after it rings—how calls are handled, how trust is built, how resistance is navigated—determines everything. That discovery led him to create the Persuasion Blueprint, a framework built on brain science, first impress...

Kris Rudeegraap is the co-founder and co-CEO of Sendoso, the largest direct mail and gifting platform in the world. Before building a company with global warehouses, a drop-ship network across continents, and $150 million in funding, Kris was a top seller who got creative when email stopped working. This conversation covers the origin story of Sendoso, the psychology of reciprocity, and why dimens...

Juan García is the co-founder of Tuio, an AI-native insurance company based in Spain. Before starting Tuio, Juan was an engineer at Cisco, a strategy consultant focused on marketing and sales, and the builder of Orange Insurance in Spain's new ventures division. That's where he saw just how broken insurance was—and decided to do something about it. This conversation covers revolutionary th...

Joe Terry and I go way back—I met him when he was CEO of Corporate Visions, and he's been on a 30-year journey studying what separates leaders who connect from those who collide. He's also the co-author of Surrender to Lead , a USA Today bestseller that reframes everything we think we know about leadership. This conversation got deep fast. We talked about the action trap—that seductive belief that...

Dramatically improve your sales effectiveness, value selling impact and sales enablement best practices by focusing on communicating. Really connecting. Frankie Kemp has one of those backgrounds that sounds made up: acting school, award-winning comedy writer, NLP practitioner, and now a communication coach for technical specialists at companies like major pharma, energy, and finance firms. She's h...

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 has been building predictive AI systems for 15 years—long before ChatGPT made it mainstream. He's a cancer survivor, serial entrepreneur, and someone who's worked with BlackRock, Blackstone, and private equity fir...

Javier Lozano Jr. on Sales and Marketing Alignment, AI, and Fixing Leaky Pipelines The Business Value Hypothesis is still the king of the sales sales strategy. And your sales people need to focus on selling with a perspective or point of view. And marketing must support this approach. If your sales and marketing teams aren't aligned on revenue, you don't have a pipeline problem — you have...

In this episode, I sit down with Drew Sechrist, the former Salesforce veteran who helped take the company from zero to $1 billion. Now the CEO of Connect the Dots, Drew is on a mission to kill the cold call forever. We discuss the "Osmosis Deficit" facing remote sales teams, why you can't close enterprise deals over Zoom, and the "LL Bean" lesson on solution selling that I...

I've been saying for years that B2B selling is broken. Alex Raymond — founder of AMplify, author of The Growth Department, and host of Account Manager Secrets — thinks account management is broken too. So naturally we had a lot to talk about. Alex has spent the last decade figuring out how companies can grow faster and more profitably through the customers they already have. And the data he br...

I recently sat down with Carole Mahoney, a self-described "hot nerd," author of Buyer First , and a woman on a mission to redeem the sales profession. Carole didn't start out loving sales; in fact, she started in marketing specifically to make salespeople obsolete. But she realized that to help small businesses grow, she had to embrace selling—not as a manipulation, but as a mechanis...

Episode Summary In this episode of Thoughts on Selling , Lee Levitt sits down with Amos Balongo —a leadership expert joining us from Hawaii who is in the business of "manufacturing leaders." We dig into a critical failure point in most organizations: the gap between Strategy and Communication. Amos argues that many leaders rely on "Positional Leadership" (people follow you beca...

Episode Summary Are your enterprise sales reps drowning in tools but starving for insight? In this episode of Thoughts on Selling , Lee Levitt sits down with Pete Smith , founder of SpotLogic and veteran sales leader, to 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 rep...

Episode Summary Is your organization guilty of the "T-Word"? In this episode of Thoughts on Selling , Lee Levitt sits down with Tom Kiernan , a veteran sales enablement practitioner (formerly of APC and Schneider Electric ), to debate the critical difference between "Sales Training" (an event) and Sales Enablement (a process). We dive into the neuroscience of selling , explorin...

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...

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. I...

Episode Summary Is your top sales rep fully caffeinated at 5:00 PM? In this episode of Thoughts on Selling , Lee Levitt sits down with Garth Fasano , an ETA (Entrepreneurship Through Acquisition) leader running a high-growth autonomous sales startup. We discuss the massive shift from traditional "Inside Sales" (humans navigating decision trees) to Agentic AI —autonomous agents that think...

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 Competit...

Episode Summary In this episode of Thoughts on Selling , Lee Levitt sits down with Sean Gannon , founder of GTMPPL (GTM People) , to answer the "unanswerable" question: Who is Sean Gannon? We dive into a refreshing (and controversial) take on Sales Leadership : why the best managers strive to make themselves obsolete . If your team can't function without you, you aren't leading—y...

Episode Summary In this episode of Thoughts on Selling , Lee Levitt geeks out with Maeve Ferguson , an ex-steeplechase jockey turned Big Four consultant and data expert. We dive deep into why the "Quiz Funnel" is dead and how Diagnostic Assessments are the new gold standard for generating high-quality leads. Maeve explains the "Delulu Factor"—how data exposes the gap between pe...

Episode Summary Sales is human work. And humans run on purpose, energy, and trust. Lee Levitt sits down with Lester Sidney , a 17-year tech sales veteran and "brother from another mother," for a raw and authentic conversation. Lester opens up about his battle with depression after leaving a company he helped build and his journey to rediscovering his "Why" through the Ikigai Fr...

Episode Summary Is your "Pipeline Problem" actually a "Data Problem"? In this episode of Thoughts on Selling , Lee Levitt sits down with Torquil Thomson , founder of The Conversion Architects , to explore a hard truth that most revenue leaders ignore: Your Go-to-Market engine is only as good as the data beneath it. Joining from Barcelona, Torquil shares astonishing stats from t...

Episode Summary In this special episode of Thoughts on Selling , Lee Levitt sits down with Gerhard Gschwandtner , founder of Selling Power Magazine . Gerhard’s story is extraordinary—from growing up in Austria to creating one of the most influential media platforms in sales history. We discuss how Curiosity , Creativity , and Courage shape every career, and why the most important question isn'...