The Thoughts on Selling™ Podcast

Lee Levitt
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  • CHAQUE SEMAINE

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. 68. From Practice to Performance; Preparing Sales Teams for an AI World

    -5 J

    68. From Practice to Performance; Preparing Sales Teams for an AI World

    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 fast, mistakes will happen, and systems thinking is essential. Upskilling & Reskilling: how organizations can build learning plans to keep talent relevant and amplify what people already do well. Applied AI in Sales: from RFP prep to simulated buyer conversations, how sales teams can use AI for deliberate practice and better customer engagement. Systems Thinking & Change Management: why AI adoption fails without clear processes, data quality, and organizational alignment. Personal Branding in the AI Era: how individuals can leverage AI to publish, create, and stay visible in a world where recommendation engines drive discovery. Ben makes a strong case: While AI won’t replace us— those who embrace it will win over those who don’t. If you’re a sales leader, enablement pro, or individual contributor wondering how to stay relevant in this exponential era of change, this conversation is for you. 👉 Connect with Ben at bentaskerai.com

    31 min

  2. 8 SEPT.

    67. Driving Behavior, Building Trust: The Playbook for Sales Leaders

    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 security startup, what would we do first? Mike breaks it down with clarity: Start with comp plans. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance. Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop. Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling. From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between 200 and 2,500 employees” isn’t a strategy). We talk about how to apply the “hive mind” to big deals by letting reps present stuck opportunities for group problem-solving. We also dig into value selling: moving past feature talk to true business outcomes — revenue growth, OPEX reduction, market expansion. Mike shares how coaching, role play, and peer-led conversations shift reps into those business-focused dialogues. A few key takeaways: Comp drives behavior. A well-built plan aligns sellers, customers, and company goals. Feedback is fuel. Win/loss analysis and customer conversations sharpen the value prop. Simplify to amplify. Tech should serve sellers, not bury them. Deliberate practice matters. Just like athletes, reps need repetition and coaching to build muscle memory. Celebrate the whole team. SEs, rev ops, legal — reward them too, not just quota carriers. This is a fun, wide-ranging conversation full of actionable ideas. If you’re leading a team, building enablement, or just want to sharpen your own selling, you’ll take something useful away. 🎧 Tune in — and let me know what resonates most. #salesleadership #salesenablement #valueselling #thoughtsonselling

    48 min

  3. 26 AOÛT

    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

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

    20 AOÛT

    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

    50 min

  5. 13 AOÛT

    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.

    45 min

  6. 5 AOÛT

    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

    37 min

  7. 28 JUIL.

    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

    43 min

  8. 15 JUIL.

    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.

    35 min
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À propos

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

Informations

  • Création
    Lee Levitt
  • Années d’activité
    2023 - 2025
  • Épisodes
    68
  • Classification
    Contenu explicite
  • Copyright
    © Lee Levitt
  • Site web de l’émission
    The Thoughts on Selling™ Podcast

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