The Advanced Selling Podcast

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

September 2, 2025 24 mins

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 sal...

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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 d...

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August 27, 2025 36 mins

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 ...

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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...

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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, consultin...

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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 som...

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August 13, 2025 12 mins

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,...

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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" a...

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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 understa...

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August 4, 2025 19 mins

In this episode of the Advanced Selling Podcast, Bill and Bryan give listeners an exclusive preview of their upcoming Insider program session on building a "platform of authority." They explain how every sales professional needs a platform where they can share valuable insights and establish themselves as an authority figure in their field.

The guys discuss what constitutes a platform (podcasts, LinkedIn, speaking engageme...

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July 30, 2025 11 mins

In this episode, Bryan dives into the critical strategy of maintaining a “virtual bench” - a curated list of talented individuals you’d love to have on your sales team. Instead of scrambling to post job ads and sift through countless resumes when a rep leaves, Bryan explains how to stay ahead by proactively building and nurturing relationships with top talent. Learn why keeping your virtual bench warm with at least one touchpoint p...

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Bill and Bryan dive deep into one of the most frustrating challenges in sales and business: resistance to change, even when that change could lead to significant growth. They explore why some decision-makers are lightning-fast adopters while others sit in limbo for months, and why even high-performing salespeople resist proven strategies that could boost their results.

The guys examine the psychology behind resistance, from the comf...

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July 21, 2025 19 mins

Summer vacation mode might be costing you your year-end goals. In this episode, Bill and Bryan dive into why your current July activities are directly shaping your Q4 results - especially if you have a 60-90 day sales cycle.

The guys share  strategies for making your year in July instead of scrambling in the fourth quarter, including how to shorten your sales cycles (think restaurant "table turns"), create a documented bac...

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In this episode, Bryan dives into a powerful yet often overlooked tool in the sales leader’s toolkit: the calendar inspection. He explains how regularly analyzing your team’s calendars can reveal dangerous pipeline gaps before they become full-blown problems.

You’ll hear why having a clear sales playbook, with numeric goals like two connector meetings and two new logo meetings scheduled 2–3 weeks out, is essential for main...

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Bill and Bryan dive deep into four powerful quotes that challenge conventional sales thinking and offer fresh perspectives on growth and success. From Buckminster Fuller's wisdom on building new models to Elon Musk's insights on optimization, this episode will make you question everything you thought you knew about scaling your business.

The guys also share personal stories, including Bryan's cautionary tale...

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Bill and Bryan tackle the crucial mid-year evaluation every salesperson should be doing right now. With two quarters behind us and a time-compressed second half ahead (thanks to holiday season), they break down practical strategies for looking backward and forward to maximize your year-end results.

Plus, Bryan shares his fascination with meter readers (yes, they still exist!), and the guys discuss why showing up authentica...

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July 2, 2025 13 mins

In this episode, Bryan unpacks a counterintuitive truth: the more structure your sales team has, the more freedom they gain. As markets grow more competitive and buyers become increasingly digital-savvy, a well-crafted sales playbook isn’t just helpful. It’s essential.

Bryan explores how playbooks streamline the sales process, remove friction, and empower reps to focus on selling, not scrambling. He also discusses how disci...

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Bill and Bryan tackle a common sales trap that costs deals and relationships: making judgments about prospects before you even sit down with them. Whether you're assuming someone can't afford your services based on company size, or writing off a "boring" CFO who might actually be your biggest champion, these snap judgments can blind you to real opportunities.

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Bill and Bryan are joined by Kevin Koharki, an accounting professor at Purdue University who specializes in teaching sales professionals how to speak the language of finance. Kevin shares his unique journey from investment banking and now helping sales teams worldwide understand how to communicate financial value to CEOs and CFOs.

Learn the difference between gross margin and operating margin, why "payback period"...

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In this episode, Bryan unpacks what makes a truly effective sales playbook - and why now is the time for sales leaders to get serious about it. He shares the key components every playbook must include: a foundational philosophy, planning elements, defined processes, contingency plans, and accountability mechanisms. Bryan spotlights the Blind Zebra Sales Operating System (BZSOS), a comprehensive set of procedures, tasks and ...

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