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The Advanced Selling Podcast
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The Advanced Selling Podcast

Author: Bill Caskey and Bryan Neale: B2B Sales Trainers

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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.

1078 Episodes
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Send us a text 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 socialization for engagement ✅ Team brag sessions that uplift ...
Send us a text 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: inventorying your unique experiences, clarifying your God-given assignment,...
Connect With Customers

Connect With Customers

2025-10-2215:15

Send us a text 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 “Connectors” — the natural networkers who love making introductions —...
Send us a text 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 understand why the language you use, the people you surround yourself wit...
Send us a text 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 during sales calls, why telling clients "I did some research" ac...
Connect With Your Team

Connect With Your Team

2025-10-0814:39

Send us a text 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 leaders: Build individual connections with reps instead of one-size-fits-all c...
Send us a text 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 everything from client prep to football officiating, and why you should tell...
Send us a text 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, coaching reps through nuanced situations, and avoiding the trap of reactive...
Send us a text 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 videos, LinkedIn article publishing (including the brilliant inte...
Send us a text In this episode, Bill and Bryan debunk one of the most persistent myths in sales training - that you can create urgency in buyers through clever tactics and techniques. They explore why deals are taking longer to close in 2025, examining both macro factors (economic uncertainty, decision-making complexity) and micro factors (changed buyer behavior, technology overload). The guys discuss how traditional urgency-creating methods like pattern interrupts and pressure tactics are no...
Send us a text Bill and Bryan explore a growing trend that's reshaping the sales landscape: the rise of "accidental salespeople." These are the technical advisors, project managers, engineers, and executives who don't have "salesperson" on their business cards but find themselves increasingly vital to the buyer-seller relationship. The guys discuss why these technically-minded professionals are becoming more important than ever, especially as traditional SDR/BDR approaches burn out prospects ...
Send us a text What happens when two conversational AI engineers realize they can't sell their own startup? They build an AI sparring partner to teach themselves—and accidentally create a game-changing sales training platform. We welcome the founders of Hyperbound.AI, Sai Guduguntla and Atul Raghunathan, who share their remarkable journey from technical founders struggling with sales to building a platform that's helping thousands of sales professionals practice and perfect their craft. In ju...
Send us a text In this early Labor Day release, Bill and Bryan dive into expert frameworks—essential tools for positioning yourself as a knowledgeable sales professional in today's market. Bill breaks down the critical video framework every salesperson needs. Learn the three-part video structure that actually gets attention: the hook that stops the scroll in the first 5 seconds, the story that keeps them engaged, and the call-to-action that drives results. Discover why social media has shifte...
Send us a text In this episode, Bryan Neale and Marcus Chan dive into the sales “red zone”—the late stage of the sales cycle where too many deals stall or fall apart. They explore how sales teams can avoid costly mistakes by addressing pricing, multi-threaded stakeholder engagement, and risk management early in the process. Marcus introduces his ADVANCE Framework, a practical tool for sales leaders to audit deals and improve forecasting accuracy. The conversation also highlights the importan...
Send us a text In this episode, Bill and Bryan shift the focus from post-sale customer experience to what they call "PX 90" - the prospect experience during the sales process. After Bryan shares a fantastic customer service call with Southwest Airlines, they dive into practical ways salespeople can go above and beyond for prospects before they become customers. The guys share practical, low-cost ways to go above and beyond for prospects that will differentiate you from the competition a...
Send us a text In this solo episode, Bill Caskey reveals one of his 12 Insider Secrets for reinventing yourself and your results: creating a mini book to establish yourself as an authority in your field. Bill shares the compelling story of how his own 20-page book "12 Bold Moves" generated a $40-50K client from a $20 purchase, demonstrating the incredible ROI potential of this positioning strategy. Whether you're in sales, consulting, or any service business, this episode shows you how to tra...
Send us a text Bill and Bryan dive into the critical balance between heart-centered selling and process-driven approaches. Sparked by a real coaching session where a top salesperson admitted "I'm not a warm guy," the guys explore why both emotional connection and systematic process are essential for sales success. They also discuss the importance of decisiveness in both sales and business relationships, and remind listeners that sometimes the best thing you can do is walk away when a prospect...
Sales Leadership Hats

Sales Leadership Hats

2025-08-1312:10

Send us a text In this episode, Bryan dives into the Sales Leadership Hats, the roles great leaders switch between to unlock performance and keep their teams moving forward. You’ll learn how to wear: The Manager Hat – Cutting through noise with data-driven decisions that point the way forward. The Coach Hat – Sharpening skills and strategies so reps get better, not just busier. The Cheerleader Hat – Sparking motivation, restoring confidence, and helping reps break through mental roadblocks...
Send us a text Bill Caskey and Bryan Neale tackle a challenge every sales professional faces: how to properly prepare for sales calls in today's digital landscape. Sparked by recent conversations with VPs of Sales about their teams going into calls "cold," Bill and Bryan break down their proven preparation framework that combines traditional research methods with cutting-edge AI tools. The guys emphasize that your "lane" as a sales professional is widening—it's no longer just about conducting...
Send us a text In this solo episode, Bill Caskey tackles the growing trust crisis facing sales professionals today. Drawing from recent research showing declining trust in businesses and institutions, Bill explores why prospects automatically assume you're going to lie to them—and why they're probably right to feel that way. He shares four practical levers you can use to build trust and stop destroying it: stop selling and start understanding, be willing to walk away when the fit isn't there,...
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Comments (5)

Jake Lewis

waste of time

Oct 8th
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Dev Cham

I love the pool story.

Dec 18th
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iTunes User

Bill and Brian are very entertaining as they speak off-the-cuff about sales and communication issues that relate to any industry - and any skill level.

Aug 30th
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iTunes User

"Advanaced" is misleading, the material will seem new only if You are new to selling. In general, this is a trite repackaing of the obvious.

Aug 30th
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iTunes User

I listened to several of these and found that ONCE YOU GET TO THE MEAT OF THE TOPIC they are pretry good. The biggest problem is wading through the chit chat that gets in the way of the meaningful dialog.

Aug 30th
Reply