The Advanced Selling Podcast
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.
Episodes
Bill Caskey breaks down the exact business planning framework from the recent ASP Insider workshop. If you haven't done your 2026 planning yet, this episode walks you through nine critical building blocks that will set you up for sustainable sales success.
From defining your vision to finding the right accountability partner, Bill covers everything you need to create a plan that actually works—not just another res...
Most business planning workshops start with vision statements and call quotas. But Bill argues there's a critical block missing from that equation: personal development. In this solo episode, he breaks down Block 8 from his 2026 Business Planning Strategy—the piece that asks not just what you need to do, but who you need to become to achieve your goals sustainably.
Bill covers four essential areas: AI literacy and...
Last week, Bill and Bryan covered mental discipline—getting your head right. This week, they shift to operational discipline: the actual behaviors and systems that high performers use to win.
This isn't about overhauling your entire life. It's about looking at your current operational system and asking: Is this working? If yes, keep rolling. If not, tweak and modify.
Bill and Bryan break down five operational ...
Bill and Bryan tackle mental discipline—but not the way you'd expect. Instead of rigid rules and forced habits, they reframe discipline as the inputs that create freedom, not constraints.
In this first part of a two-part series, they explore the mental shifts that separate high performers from the rest: quieting your mind, embracing possibility thinking, getting comfortable with failure, and continuously feeding y...
In this episode of The Advanced Selling Podcast, Bryan Neale sits down with sales compensation expert Chris Goff, better known across the industry as “The Sales Comp Guy.” With deep experience in sales operations, territory optimization, and comp plan design, Chris brings a rare, holistic perspective to one of the most emotionally charged topics in sales: how sellers get paid.
Together, Bryan and Chris unpack why compe...
Part two of our macro vs. micro skills series—and this one gets tactical.
Bill and Bryan dive into the small, incremental skills that most salespeople overlook but that separate pros from amateurs. These aren't the big-picture capabilities; they're the in-the-moment moves that determine whether your sales calls actually go anywhere.
The guys cover the courage to stop and clarify when something's confusing...
Most salespeople waste their first meeting covering basics that could've been handled beforehand. Bill introduces a game-changing digital asset: the introductory video—a 5-minute pre-meeting video that positions you as a credible problem-solver before the conversation even starts.
In this episode, Bill breaks down the exact structure of an effective introductory video, including the hook that grabs attention in 10...
Bill and Bryan break down the difference between macro and micro sales skills—and why both matter more than you think. Inspired by a prospect who called out his own team for not asking clarifying questions, this episode explores the big-picture capabilities that separate average performers from top producers.
They cover essential macro skills including strategic planning (with outcomes AND behaviors), reverse engineeri...
Bill Caskey follows up on last week's deep dive by sharing insights from coaching a high-performing salesperson who's hitting the limits of process-driven selling.
He reveals why even the best sales process isn't enough—you must show up authentically and have the courage to disqualify prospects who aren't truly committed.
Through a compelling coaching story, Caskey explains how being grounded in wh...
In this episode of The Advanced Selling Podcast, Bryan Neale sits down with longtime friend and sales veteran Vince Beese, a fractional CRO and sales coach with over 25 years of B2B enterprise experience and five successful exits under his belt. Together, they dive deep into “Red Zone Selling:” a framework inspired by football that helps sellers stay focused, avoid complacency, and close more deals when it matters mos...
Are you uncomfortable talking about money with prospects? You're not alone. In this episode, Bill and Bryan tackle one of the biggest challenges sales professionals face: bringing up price, cost, and economic conversations without the anxiety and uncertainty that usually comes with it.
Whether you're dealing with technology sales, competitive situations, or demonstrating clear ROI, this episode give...
In this episode, Bill and Bryan continue their conversation on sales culture with actionable tactics you can implement immediately. Whether you're building team culture or your personal approach, these strategies will help you create intentional, high-performing environments.
What You'll Learn:
✅ How to build customer relationship culture through strategic meetups
✅ The power of book clubs and team socializat...
Bill Caskey poses a challenging question: If you disappeared from your prospect's world tomorrow, would they feel the loss?
In this introspective solo episode, he explores the "invisible dimension" of sales—the deeper level where prospects evaluate not just your skills and process, but your unique presence and purpose. Caskey shares three powerful practices for connecting with your authentic self: inven...
In this episode, Bryan Neale from Blind Zebra shares a tactical framework for building meaningful customer connections — one rooted in strategy, generosity, and intentional networking. He explains why great salespeople move beyond vague Ideal Customer Profiles (ICPs) to create “conquest account lists” that name specific people they want introductions to.
Bryan also challenges listeners to identify at least 20 “Connecto...
Bill and Bryan kick off a two-part series on sales culture by sharing what they've observed from years of working inside dozens of organizations. In this episode, they explore the difference between surface-level culture (the pictures on the wall) and the real culture you can feel in the air.
Whether you lead a sales team or carry your own quota, this episode will help you see culture in tangible ways—and understa...
In part two of their AI series, Bill and Bryan get specific—sharing real examples of how they use AI in their daily sales work. Bill walks through actual ChatGPT conversations for client prep (including a memorable moment when the AI got it wrong about an ESOP), while Bryan demonstrates how he uses Claude to research prospects and create strategic talking points.
You'll hear how they validate AI-generated research...
In this episode, Bryan explores why the best sales leaders focus as much on connecting with their people as they do on connecting with their customers.
Sales is often seen as an individual sport - everyone chasing their own numbers and commissions. But the real magic happens when leaders take time to understand each team member’s unique motivations and coach them accordingly.
Bryan shares how great l...
Bill and Bryan dive into how they're actually using AI in their daily sales work—no hype, just practical applications. In part one of this two-part series, they share their number one use case: preparation for sales calls, including researching companies, understanding buyer contexts, and making discovery more efficient.
You'll learn why Bill treats AI like an executive assistant, how Bryan uses it for everyt...
In this episode, Bryan is joined by John Barrows to talk about the high-stakes final stage of the sales process, where deals are either won or lost. Together, they explore why so many sales teams stumble here, often resorting to last-minute discounts or high-pressure tactics driven by forecast anxiety.
Bryan and John share strategies to keep control of the process, including engaging procurement early, coachi...
Tired of perfecting your sales skills but struggling to get in front of the right people? Bill and Bryan tackle the universal challenge every B2B professional faces: visibility. Using a real client case study from the tax law industry, they reveal why traditional cold calling is dead and share actionable strategies to become visible where your prospects are already looking.
Discover how to leverage weekly insight video...
Popular Podcasts
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The official podcast of comedian Joe Rogan.
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Listen to 'The Bobby Bones Show' by downloading the daily full replay.
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com