The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainers
  • 4.3 (345)
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Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges you face daily: prospecting, overcoming buyer resistance, pricing strategies, cold calling, deal coaching, and building long-term client relationships. Whether you're a sales professional, manager, or leader, you'll discover how to shift your mindset, leverage your natural talents, and create sustainable sales success. From mastering sales communication and handling RFPs to understanding buyer psychology and effective positioning, Bill and Bryan cover everything that actually works in modern B2B sales.

  1. The Best Sales Gifts Nobody Buys You

    2D AGO

    The Best Sales Gifts Nobody Buys You

    Send a text It's Bill's birthday — and that means one thing: it's time to talk about gifts. But not the usual Amazon cards and polka dot sweaters. Bill and Bryan dig into the sales gifts worth actually giving yourself: the mindset shifts, investments, habits, and tools that compound over time. In this episode, you'll hear about the gift of applying abundance thinking to your sales life, why investing in yourself is the one gift no one else will buy you, the power of true free time (and why refusing to take it is just inflated self-importance), building a personal brand by sharing real problems and solutions, becoming a generalist in the AI age, and seeing modern tools — your CRM, LinkedIn, AI — as gifts rather than burdens. Whether it's your birthday or not, this episode is a reminder to stop waiting for your company to invest in you and start doing it yourself. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com Turn your content into clients with the proven roadmap — join Insider today at advancedsellingpodcast.com/insider

    21 min
  2. AI as a Sales Tool, Not a Salesperson with Kayla Kurtz

    FEB 25

    AI as a Sales Tool, Not a Salesperson with Kayla Kurtz

    Send a text In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Kayla Kurtz, VP of Sales and VP of Business Development at Forthea, for a focused conversation on how AI is reshaping modern sales. Kayla shares how aligning sales and marketing improves lead quality and eliminates the “bad lead” blame game, before diving into practical ways sellers can use AI tools like ChatGPT and Copilot to refine emails, personalize outreach, and prepare for complex conversations. Bryan and Kayla also address the risks of inaccurate AI outputs and why positioning insights as questions, and not facts, protects credibility. They close by exploring how buyers are using AI to research vendors and negotiate more strategically, challenging sales teams to elevate their preparation and technical depth. The episode reframes AI as a tool that sharpens execution without replacing relationship-driven selling. ______ Curious about certification in the Blind Zebra Sales Operating System? Learn more here. Turn your content into clients with the proven roadmap — join Insider today at advancedsellingpodcast.com/insider

    32 min
  3. From Content to Conquest

    FEB 24

    From Content to Conquest

    Send a text Bill and Bryan are giving you a preview of the March 6th ASP Insider session — and it's one you don't want to miss. The topic is From Content to Conquest, but this isn't a social media training. It's about what you know, what you believe, and how you package your expertise so prospects say, "I want to know more." Before diving into the March session, Bill and Bryan walk through the perspective shifts that have to happen first — because you can know exactly what to do and still not do it. The missing ingredient is almost always how you see things. Plus, Bryan shares how the Mental Health for Salespeople series resonated far beyond the sales world — and what that buzz means for upcoming episodes. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com Turn your content into clients with the proven roadmap — join Insider today at advancedsellingpodcast.com/insider

    20 min
  4. Why Collaboration Beats Closing Tactics Every Time

    FEB 16

    Why Collaboration Beats Closing Tactics Every Time

    Send a text What if your entire sales process—from networking to contract signing—was built on collaboration instead of persuasion?  In this episode, Bill and Bryan break down what real collaboration looks like at every stage: pre-sale networking, early conversations, mid-stage resistance, and closing deals. You'll discover why most salespeople avoid collaboration (they're afraid of conflict), how to audit your sales process for collaborative moments, and the simple phrase that sets the tone from day one.  Bill shares a client story about refusing to send a proposal until they collaborated on unanswered questions—and how it built immediate trust.  Whether you're stuck in transactional mode or ready to differentiate yourself completely, this episode gives you a new through line that actually works. Join the conversation: AdvancedSellingPodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    20 min
  5. Saving Sales Time with Smarter Routes ft. Steve Benson

    FEB 11

    Saving Sales Time with Smarter Routes ft. Steve Benson

    Send a text In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Steve Benson, founder of Badger Maps, for a conversation on why outside sales teams are often overlooked by modern sales technology — and what happens when tools are finally built with field sellers in mind. Bryan and Steve dig into the realities of territory design and route planning, calling out how many sales leaders still rely on gut feel and educated guesses when structuring territories. Steve explains how Badger Maps and Badger Align help sales teams visualize customers geographically, balance territories using real data, and create more efficient routes that lead to more meetings and measurable sales lift. They also explore why mobile-friendly CRM tools matter so much for outside sellers, and how removing friction from data entry in the field directly impacts performance. The conversation expands into Badger Maps’ broader platform, including lead routing, geographic insights, and performance tracking, before Steve shares the origin story behind the product — a firsthand realization that sales data is far more powerful when you can see it on a map. _______ Curious about certification in the Blind Zebra Sales Operating System? Learn more here.

    27 min
  6. Is Your Through Line Costing You Business?

    FEB 10

    Is Your Through Line Costing You Business?

    Send a text What can Charlie Puth's collaboration with Kenny G for the Super Bowl national anthem teach us about sales? More than you'd think. Bill and Bryan break down the story of how Charlie Puth persistently pursued Kenny G—not through aggressive follow-ups, but through generous, creative demonstrations of value. He sent tracks. He added a choir. He painted the picture so vividly that Kenny G couldn't help but respond. The sales lessons are everywhere: Clean intention enables authentic persistence. Information isn't proprietary anymore, so stop withholding it. Collaboration beats competition. And most importantly, your "through line"—the underlying driver of your sales process—might be sabotaging your success. Most sales methodologies operate on a selfish through line: What do I need to say or do to get the deal? That approach creates manipulation, defensiveness, and resistance. But what if collaboration was your through line instead? Join the conversation: AdvancedSellingPodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

    19 min
  7. Be the Guide Your Customers Are Craving

    FEB 6

    Be the Guide Your Customers Are Craving

    Send a text Bill Caskey explores the most important question in sales: What is your role in the buyer-seller dance? In this solo episode, Bill breaks down the Guide Model—a three-part framework that transforms how you show up with customers. Instead of selling to people who don't need what you offer, you become the guide that customers are craving. If you've ever wondered why buyers don't trust you or why price becomes the sticking point, this episode reveals what's really happening—and how to fix it. This is part 2 of a 2-part series on how to be a guide. 🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

    7 min
  8. Mental Health in Sales: Movement Creates Momentum

    FEB 2

    Mental Health in Sales: Movement Creates Momentum

    Send a text In the final episode of our mental health in sales series, Bill and Bryan tackle a truth most sellers ignore: you can't think your way out of a slump—you have to move your way out. Drawing from Scott Galloway's "get out of the house" philosophy and real client stories, they explore how physical action—whether it's actual exercise or the behavioral action of getting out and connecting with people—breaks the isolation cycle that feeds sales depression. Bill shares a coaching win where an engineer went from zero prospecting hours to booking two appointments just by reaching out to reconnect with old contacts. No pitch, no agenda—just human connection.  Whether you're feeling stuck, isolated, or just going through the motions, this episode delivers the kick you need to stop overthinking and start moving. This is Part 4 of our Mental Health in Sales series. Find all episodes at https://vault.advancedsellingpodcast.com/mental-health-in-sales Join the conversation: AdvancedSellingPodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider Turn your content into clients with the proven roadmap — join Insider today at advancedsellingpodcast.com/insider

    25 min
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4.3
out of 5
345 Ratings

About

Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges you face daily: prospecting, overcoming buyer resistance, pricing strategies, cold calling, deal coaching, and building long-term client relationships. Whether you're a sales professional, manager, or leader, you'll discover how to shift your mindset, leverage your natural talents, and create sustainable sales success. From mastering sales communication and handling RFPs to understanding buyer psychology and effective positioning, Bill and Bryan cover everything that actually works in modern B2B sales.

Information

  • Creator
    Bill Caskey and Bryan Neale: B2B Sales Trainers
  • Years Active
    2006 - 2026
  • Episodes
    1.1K
  • Rating
    Clean
  • Copyright
    © 2026 The Advanced Selling Podcast
  • Show Website
    The Advanced Selling Podcast

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