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

Episode Summary In this episode of Thoughts on Selling , Lee Levitt sits down with Lauren Bailey , one of the most dynamic voices in modern sales leadership. She is the founder of Factor 8 (inside sales training), #GirlsClub (empowering women in revenue), and Legacy VIP . What starts as a conversation about sales tactics quickly turns into something deeper—a raw, funny, and inspiring dialogue abou...

Episode Summary Is your sales pitch a rehearsed monologue or a collaborative improv scene? In this episode of Thoughts on Selling , Lee Levitt sits down with Kevin Hubschmann , former enterprise rep turned comedian and founder of Laugh. Events . We dig into the fascinating parallels between stand-up comedy and enterprise sales. Kevin shares his story of balancing daytime sales calls with nighttime...

Episode Summary Is sales a science or a performance art? In this episode of Thoughts on Selling , Lee Levitt sits down with Jake Isham , a filmmaker, creative director, and founder of Creative Minds Agency . Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and eventually became what he calls an "accidental marketer." We dig deep...

Episode Summary Is sales a business process or a psychological one? In this episode of Thoughts on Selling , Lee Levitt sits down with Laura Keith , CEO of Hive Perform and Hive Learning (and self-proclaimed "Chief Entertainment Officer" to three kids). Laura’s journey is fascinating: she never planned to work in sales. She studied psychology. But she quickly realized that the traits req...

Episode Summary In a world where AI can write your emails, generate your scripts, and predict your forecast, is there anything left for the human seller? Lee sits down with Jeff Kirchick —sales leader, author, and unapologetic advocate for authenticity—to answer that question. Jeff’s journey is unconventional: from an English major and aspiring screenwriter to a startup sales leader closing seven-...

In this episode of Thoughts on Selling , I sit down with David Donlan , VP of Sales at IP Co-Pilot, longtime tech sales leader, and passionate mentor for the next generation of sales professionals. David and I cover a wide range of topics — from his early days upselling azaleas with fertilizer at age 15 to shaping sales teams at HubSpot, and now building a company that helps innovators protect and...

In this episode of Thoughts on Selling , I sit down with Ted McKenna — researcher, author, and co-creator of some of the most influential sales frameworks of the past two decades. Ted has been behind The Challenger Sale , The JOLT Effect , and most recently, The Activator Advantage . We dive into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and wh...

In this episode of Thoughts on Selling , I sit down with AI strategist and workforce transformation expert Ben Tasker . Ben has spent over a decade helping organizations harness AI not just as a shiny tool, but as a way to amplify human abilities through upskilling, reskilling, and smarter systems thinking. We dive into: The “AI Between Times” : why we’re in a transition period where adoption is f...

In this episode of Thoughts on Selling , I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams. We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a...

In this episode, I sit down with Matt Wilkinson — life sciences marketer turned AI strategy partner, Visiting Fellow at Cranfield School of Management, and board member at the Association of Key Account Management. Matt brings a sharp lens to the challenges of sales and marketing alignment, the rise of AI in B2B, and what it really takes to create customers in today’s environment. We cover a wide...

Tracy Linne, an experienced sales leader and strategist, joins me for a powerful conversation on the intersection of leadership, clarity, and sales performance for this episode of the Thoughts on Selling podcast. Tracy emphasizes the role of leaders in shaping not just strategy but belief within teams. Our discussion covers the importance of creating clarity in complex environments, the necessity...

In this episode of Thoughts on Selling , I get to sit down with the incredible Kaivona Parker —the Unboring Sales Specialist —and let me tell you, she lives up to the name. We talk about what it really means to sell without the mask on. Kaivona shares her journey from breaking into tech sales to becoming a voice for underrepresented sellers, and how she’s using enablement to create safe spaces whe...

In this episode of the Thoughts on Selling podcast, I sit down with Kerry Curran — go-to-market strategist, agency veteran, and fierce advocate for customer-centric marketing and sales. Kerry brings a unique blend of analytical rigor and empathetic leadership to every conversation, and this one’s no different. We dig into what it really means to be customer-obsessed — and how that obsession shows...

In this episode of the Thoughts on Selling podcast, I sit down with Dre Baldwin — entrepreneur, keynote speaker, and former pro basketball player — to talk about the intersection of mindset, sales, and performance. Dre brings an intense, no-nonsense perspective to the world of business and selling, grounded in his experience hustling his way from overlooked high school athlete to a nine-year pro b...

Episode Summary Are you selling, or are you just performing? In this episode of Thoughts on Selling , Lee Levitt sits down with the fabulous Stacy Bishop to cover some serious ground—from Midwest values and fintech sales to the surprising wisdom of improv comedy. If you have ever tried on a "sales persona" like an ill-fitting suit (and watched it fail), this episode is for you. We discus...

For this episode I’m joined by Vance Morris—a guy whose journey goes from rock bands to Disney to running premium home services, and now helping businesses “Disney-fy” their customer experience. And let me tell you, the parallels to sales are everywhere. If you’re in sales and think “customer experience” doesn’t apply to you—this episode will change your mind. ✅ Systems Create Freedom… and Room f...

This episode was an absolute blast. I’m joined by Guy Rubin, CEO of Ebsta, who brings not just revenue intelligence expertise—but also a love of physics, football (the British kind), and skiing—to the conversation. We talk about the problem that’s plagued sales teams for decades: data that’s incomplete, inaccurate, or invisible. Guy shares how Ebsta evolved from solving Salesforce data issues into...

In this episode of Thoughts on Selling , I sit down with Britt White—sales leader, edtech evangelist, former VP of Sales at SmartPass, and a force of nature when it comes to bringing passion to work. This isn’t a scripted “how-to” chat. It’s a real conversation between two humans unpacking what it means to love what you do—and how that love shows up (or doesn’t) in sales, leadership, and culture....

On this episode of Thoughts on Selling , I sit down with Jackie Retig, a passionate sales enablement leader and COO at EnableWorks. Jackie recently made the leap into entrepreneurship after years in the tech space, and she brings a grounded, practical perspective to what it really takes to build consistent, scalable sales teams. We get into why enablement is more than just onboarding and training—...

In this episode of Thoughts on Selling , I sit down with Borja Cuan, co-founder of Four15 Digital, to talk all things demand gen, agency life, and what it takes to deliver results—not just leads. Borja's been in the digital marketing game since the late '90s, and his perspective on execution, transparency, and the importance of asking the right questions is both refreshing and, frankly, necessary...

In this episode, my good friend Alistair Corrie and I take a deep dive into toe topics of mindset, mastery, and how we get out of our own way—whether in selling, sports, leadership, or life. Alistair draws from a range of disciplines—The Inner game, Zen and the Art of Motorcycle Maintenance, martial arts concepts like Shu-Ha-Ri-Kokoro, Viktor Frankl’s logotherapy, and more—to explore what mastery...

For this episode, I had the pleasure of chatting with David Kirkdorffer — marketing veteran, recording artist, hat enthusiast, and self-proclaimed connective tissue between sales and marketing. We talked all about how sales and marketing can actually get along , the evolution of enablement, and what happens when buyers (and AI) start running the show. 🔑 Key Takeaways from Our Conversation: Sales...

In this episode, I had a great conversation with Tim Bradley, founder of Pennant—a video marketing firm that’s laser-focused on helping companies improve conversion rates in the middle of the funnel. Tim’s all about storytelling, yes—but with a clear eye on how that story supports sales performance . We talked a lot about the line between marketing and sales enablement , and how the best content—e...

In this episode of Thoughts on Selling , I sit down with sales coach and former VP of Sales, Shane Jamison, to talk about the real work behind sustainable sales—coaching to the numbers, managing pipeline pressure without compromising relationships, and becoming the guide your customer needs. We dive into what it means to stay authentic when management wants pull-ins, how to balance urgency with tr...

In this episode of the Thoughts on Selling podcast, I welcome Steven Ethridge, an accomplished sales trainer, coach, and expert in Neuro-Linguistic Programming (NLP). Our conversation dives into the pivotal roles that mindset and intentional communication play in driving meaningful sales outcomes. Steven shares his structured two-part methodology: Sales Mindset Self-Mastery and his NLP-based Five-...