The Thoughts on Selling™ Podcast

Lee Levitt
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The Thoughts On Selling™ podcast explores the issues in driving enterprise sales revenue through effective pipeline development, account planning and sales performance management. Join us to learn best practices and things to avoid, with the goal of maximizing the account penetration, customer share of wallet, customer satisfaction and sales productivity of your organization. For more information and to browse the podcast library, please visit http://podcast.thoughtsonselling.com

  1. 8월 26일

    66. 10,000 AI Conversations vs. One Human One: Which WIns?

    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 range of topics, from why account-based approaches are so powerful when done right, to how culture inside organizations shapes buying behavior, to the shifting role of brand and trust in an AI-driven world. Some key takeaways from our conversation: Sales + Marketing must share the same North Star. Vanity metrics and siloed KPIs create friction instead of customers. Account-based strategy works best when sales and marketing co-create it. Alignment starts with shared target accounts, shared narratives, and shared wins. AI is rewriting the buying journey. Buyers come to conversations armed with custom, AI-generated insights — which means sellers need a point of view, not just information. Brand still matters. Even in a digital-first, bot-enabled world, strong brands reduce perceived risk and influence decisions. Know your customer deeply. Visit them, learn their culture, and align your story to their mission — whether that’s patient outcomes, revenue growth, or reducing risk. Trust and human connection win. Efficiency is not effectiveness; one meaningful, risk-reducing conversation beats 10,000 shallow ones. Matt’s blend of academic insight, practical experience, and stories (yes, even about coffee makers!) makes this a conversation packed with perspective for anyone navigating modern B2B sales and marketing. 🎧 Give it a listen — and let me know what resonates with you. #sales #marketing #AI #accountbasedmarketing #thoughtsonselling

    35분
  2. 65. Sales with Purpose: Creating Cultures of Trust and Growth

    8월 20일

    65. Sales with Purpose: Creating Cultures of Trust and Growth

    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 of building trust as the foundation for growth, and why adaptability is a hallmark of modern sales leadership. Key insights include: Sales as an energy exchange. Leaders must embody the inspiration they want their teams to deliver. The power of simplicity. Clear direction removes friction and accelerates execution. Trust as a multiplier. High-trust environments drive accountability, creativity, and resilience. Leadership by example. The behaviors modeled by leaders set the cultural tone. This episode is particularly relevant for sales executives, revenue leaders, and anyone navigating the challenges of leading high-performing teams in dynamic markets. 🎧 Tune in and discover how Tracy’s insights can sharpen your leadership approach. #salesstrategy #leadership #salesenablement #growthmindset #thoughtsonselling

    50분

  3. 8월 13일

    64. Authenticity: Sales, Storytelling and Showing Up Real with Kaivona Parker

    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 where people can bring their whole selves to work. We swap stories on improv, authenticity, faith, motherhood, and the mental game of sales—and how all of it ties back to showing up real in every conversation. 💡 My Favorite Takeaways Authenticity wins every time—but you have to give yourself permission to show it. Sales is improv—every objection is just an offer. Storytelling > scripts—the right story can make the sale without ever talking specs. Great leaders create space for others to be themselves. Your reps’ story matters—start onboarding there, not in the LMS. 🔥 Why This Conversation Stuck With Me Kaivona said something that’s still ringing in my ears: “When you hold back yourself, you hold back your success.” That’s it. That’s the post. Too many sales pros are still trying to be someone else’s version of “professional.” This episode is all about breaking that pattern—and why it’s good for both your career and your customers. If you’ve ever felt like you had to “play a role” in sales, this one’s for you. Give it a listen, and let me know what lands with you most.

    45분

  4. 8월 5일

    63. Data, Decisions, & the Human Side of Sales with Kerry Curran

    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 up in everything from messaging to enablement to revenue alignment. Kerry shares insights from her time leading strategy at agency and consulting firms, and we talk about how B2B sellers can learn a lot from B2C when it comes to creating emotional resonance with buyers. Key takeaways from our conversation: The buyer is always human. Even in the most technical enterprise sale, people buy with emotion and justify with logic. Marketing and sales must align on customer understanding. ICP, messaging, and content strategy all depend on shared insight. Storytelling isn’t fluffy — it’s functional. Sellers need to connect the dots and craft narratives that make buyers feel seen. Data informs, but doesn’t replace, intuition. The best GTM leaders balance analytics with experience. Success starts with curiosity. The most impactful sellers and strategists ask better questions — of customers and of themselves. This one’s packed with wisdom for marketers, sellers, and enablement pros who want to create deeper alignment and stronger relationships with their buyers. 🎧 Give it a listen — and let me know what resonates with you. #customerobsession #salesandmarketingalignment #gtmstrategy #thoughtsonselling #b2bsales #storyselling

    37분

  5. 7월 28일

    62. Work On Your Game: Mindset, Discipline, and the Truth About Selling

    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 basketball career overseas. And he applies the same discipline, strategy, and mindset to his work now as a content creator, coach, and sales leader. We talk about: Why confidence is a decision, not a feeling How discipline beats motivation (every time) The parallels between cold outreach and showing up to practice How to handle rejection, objections, and ghosting without taking it personally What salespeople can learn from athletes about preparation and mental conditioning Dre also breaks down why many reps overthink instead of act, and why clarity + execution = momentum. He calls out the trap of waiting for permission, and urges sales pros to trust their skills, trust their reps, and get in the game. If you're in sales and struggling with consistency, rejection, or just getting out of your own head — this one's for you. 🎧 Give it a listen and let me know what landed. #salesmindset #confidence #salesperformance #thoughtsonselling #workonyourgame

    43분

  6. 7월 15일

    61. Selling Without the Mask: Authenticity, Improv, and the Inner Game of Sales

    On this episode of Thoughts On Selling, I’m joined by the fabulous Stacy Bishop, and wow, we cover some ground. From Midwest values and fintech sales to improv comedy and why your brain should zip it sometimes—we’re bringing the laughs and the lessons. If you’ve ever wondered whether you’re selling—or just waiting to talk—or struggled with how to pivot in a sales call without face-planting, this one’s for you. Here’s a taste of what we dig into: 🎯 Authenticity over ego Stacy shares how growing up in the Midwest shaped her career in banking and fintech sales—and how being real beats trying to be someone else. I confess to the times I tried on other people’s “sales personas” like ill-fitting suits. (Spoiler: It didn’t work.) We talk about dropping the mask and just being you—even when you’re the only woman in the boardroom. 🎭 Improv wisdom for sellers Why every statement in a conversation is an offer, not an objection. The magic of “Yes, and…” How I learned from improv (and my dog) that being present changes everything in sales. 🧠 The inner game of selling Why you can’t think your way through a tennis swing—or a sales pivot. “Go slow to go fast”—what racing, parenting, and selling all have in common. Stacy and I bond over how little time salespeople actually get to practice their craft—and why it’s killing deals. 🚀 Practical tips you can steal right now: Ask your customers why they’ve stayed with their company for 25 years—you’ll open doors you never expected. When you hear “no,” remember—it’s an offer, not the end of the road. Pivot like a pro. Don’t assume how people will react. Give them the chance to surprise you. When the customer starts nodding and saying yes… STOP TALKING. Zip it! Stacy leaves us with two killer reminders: ✅ Be your authentic self—even (especially) in sales.✅ Follow up. And then follow up again. Because today’s “not now” might be tomorrow’s “hell yes.” Find Stacy on LinkedIn here — she’s all about helping other sellers figure out how to navigate this wild world of sales without losing their sanity. Key Takeaways: Sales is human-to-human. Authenticity wins every time. Improv teaches incredible sales lessons: be present, pivot fast, and say “yes, and.” Practice isn’t optional—it’s how you go from “good” to “unconsciously great.” Go slow to go fast. Seriously. Drop the mask. Be yourself. It’s way less exhausting. Quotable Moments: “Give me the opportunity to surprise you.” — Stacy Bishop “Are you being of service… or serving your ego?” — Lee Levitt “Every statement is an offer, not an objection.” — Lee Levitt This episode is a blast. It’s full of laughs, real talk, and enough practical nuggets to fuel your next dozen sales calls. Thanks for tuning in, friends—and as always, go out there and sell like yourself.

    35분

  7. 7월 8일

    60. Creating your customer experience: Lessons from Disney and beyond

    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 for DelightAt Disney, every detail is scripted and systematized so cast members can focus on the magic. It’s the same in sales: if you’ve got your basics dialed in—your research, your process, your CRM—you’re free to actually connect with buyers and deliver value instead of scrambling. ✅ First and Last Touches Make or Break YouDisney obsesses over the first impression (parking, music, greetings) and the final moment (fireworks). As salespeople, our first touch is the brand experience. Whether it’s an email, call, or meeting, buyers decide quickly whether they trust us—or not. And how we end a conversation matters just as much. ✅ Experiences Beat TransactionsVance’s carpet cleaning business sends a $5 gift box to every customer—just a small delight that led to a 26% increase in higher-tier sales. In sales, it might be a thoughtful follow-up, a handwritten note, or sending a “lumpy mail” package that stands out. It’s about making buyers say: “These people are different.” ✅ Don’t Race to the BottomSalespeople who lead with discounts or lowest price become commodities. Vance urges businesses to charge for the experience they deliver. In sales, we need to sell on value, not price—and confidently walk away from bad deals. ✅ Retention > AcquisitionIt costs Vance $135 to get a new customer, but only $22 a year to keep one. Salespeople too often chase new logos and forget that existing customers are way more profitable. Delight your customers, and they’ll stay—and buy more. ✅ Delight = RevenueDisney servers giving FastPasses to stressed-out families is a perfect metaphor for sales: solve problems proactively, even ones that “aren’t your department.” It builds loyalty, trust, and bigger deals. We also dig into: Creative ways to stand out (cowbells, coffee mailers, even rubber feet for “getting a foot in the door”) Why salespeople should never be boring Why “what would Grandma do?” might be the best sales strategy ever The real meaning of primacy and recency in sales conversations Why you should never assume buyers think like you do Bottom line: As salespeople, we’re in the experience business. Every touchpoint is your chance to create delight—and separate yourself from the crowd. Get more from Vance:→ Grab his free guide: 52 Ways to Wow Without Breaking the Bank→ Check out his business and Disney bootcamps: deliverservicenow.com Thanks, Vance, for an awesome conversation that’s pure gold for anyone selling anything! #Sales #CustomerExperience #RevenueGrowth #DisneySecrets #ThoughtsOnSelling

    46분

  8. 6월 30일

    59. From Gut Feel to Revenue Intelligence: Sales in the Age of Data

    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 building a revenue intelligence platform that helps companies truly understand what’s driving wins—and where deals stall. Some of the big takeaways from our chat: ✅ Your CRM isn’t the whole truth. Email, calendars, and “hidden” stakeholder interactions hold critical data about deals. Mining that signals where opportunities are real—and where they’re just wishful thinking. ✅ Sales is the last department to get truly data-driven. Imagine marketing running on gut feel—it’s unthinkable. Sales orgs need to catch up. ✅ B and C players can level up. Guy makes a strong case that coaching and data insights—not just “cutting the bottom third”—can help more reps replicate A-player behavior. ✅ Pipeline inspection needs consistency AND context. It’s not enough to follow a checklist; you need to tie activities and engagement to outcomes you can actually prove. ✅ Discovery is co-creation. We both rant (a bit) about how discovery is more than just running through questions. It’s a collaborative process that evolves throughout the deal. ✅ Retention > new logos (sometimes). Ebsta’s data shows that in B2B SaaS, existing customers generated more new revenue than new logos last year. The key? C-level engagement during QBRs. We geek out about pipeline forecasting, coaching, the role of RevOps, and why “happy ears” still kill deals. Guy also shares fascinating benchmarks—like how engaging six stakeholders (including finance and a C-level exec) in stage two of a deal can nearly triple win rates. Guy’s message is clear: Sales can (and must) become data-driven if we want predictable, scalable growth. Check it out—and let me know which insights resonate with you most! #sales #revenuestrategy #salescoaching #salesenablement #revenueintelligence #thoughtsonselling

    32분
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The Thoughts On Selling™ podcast explores the issues in driving enterprise sales revenue through effective pipeline development, account planning and sales performance management. Join us to learn best practices and things to avoid, with the goal of maximizing the account penetration, customer share of wallet, customer satisfaction and sales productivity of your organization. For more information and to browse the podcast library, please visit http://podcast.thoughtsonselling.com

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