The Bill Caskey Podcast: High Impact Sales Training for Sellers and Leaders

Bill Caskey
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  • UPDATED WEEKLY

Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business.Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable insights and actionable advice that will help you build your skills and think differently about the profession of selling.Whether you're a seasoned sales professional or just starting out in your sales career, The Bill Caskey Podcast has something for you. So, join us every week as we explore the latest trends, techniques, and strategies for driving sales growth and success.To learn more about Bill Caskey and his work, visit www.billcaskey.com or follow him on LinkedIn at https://www.linkedin.com/in/billcaskey/.

  1. 5 Lessons from Front-Line B2B Professionals (And How You Can Apply It Today)

    NOV 5

    5 Lessons from Front-Line B2B Professionals (And How You Can Apply It Today)

    What happens when experienced B2B sales professionals—many with engineering backgrounds—spend six months mastering consultative selling techniques? In this episode, I share the five most impactful lessons from a recent training program with high-end hydraulic and timing solutions salespeople. You'll discover why being mindful of the "okay vs. not okay" dynamic transforms customer interactions, how upfront agreements and detachment create better outcomes, and the critical importance of operating on two levels simultaneously—being in the conversation while also observing it. Whether you're selling complex solutions or leading a sales team, these field-tested insights will help you connect more authentically with prospects and close more deals. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com. 🎧 Ready to absorb these bold moves while on the go? Download the complete audiobook version at 12boldmoves.com/audiobook and transform your sales results during your commute, workout, or downtime.

    14 min
  2. Finding Yourself in Business with Jason Leister

    OCT 3

    Finding Yourself in Business with Jason Leister

    In this episode, Bill Caskey sits down with marketing expert and recovering musician Jason Leister to explore a topic that sits beneath the surface of most business conversations: the power of being yourself. Jason shares his journey from being a "straight-A sheep" who followed all the rules to discovering that the only person he hadn't tried being in business was actually himself. The conversation digs into why we're taught to focus on what we want to do rather than who we want to be, and how that misdirection costs us years of detours, therapy, and unfulfilled projects. If you've ever felt like you're operating at a fraction of your potential, or you're tired of being everyone except yourself, this conversation offers a refreshing perspective on building a business—and a life—that actually fits who you are. Subscribe to Jason's daily newsletter at JasonLeister.co for continued insights on becoming more fully yourself in business. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com. 🎧 Ready to absorb these bold moves while on the go? Download the complete audiobook version at 12boldmoves.com/audiobook and transform your sales results during your commute, workout, or downtime.

    25 min
  3. Remembering Charlie Kirk: Lessons in Being Fearless & Empowered

    SEP 17

    Remembering Charlie Kirk: Lessons in Being Fearless & Empowered

    In this heartfelt tribute episode, we pause to reflect on the life and legacy of Charlie Kirk, the founder of Turning Point USA who was tragically taken from us far too soon. While this isn't a political analysis, it's a personal reflection on what we can learn from Charlie's approach to life and leadership. This episode explores the leadership lessons we can all take from Charlie's life: his courage to engage in difficult spaces, his ability to stay on message, his mastery of media platforms, and most importantly, his dedication to serving as a voice of hope for young people who felt forgotten by society. Whether you agreed with his politics or not, there's no denying Charlie Kirk's massive impact on American youth and his role as a devoted father and husband. Join us as we honor his memory and reflect on how we can better support the young people in our own lives during these challenging times. This is a one-time tribute episode from someone who admired Charlie's communication skills and dedication to youth empowerment, regardless of political affiliation.

    7 min
  4. How to Get in the Right Position to Close More Deals

    AUG 28

    How to Get in the Right Position to Close More Deals

    One of the biggest problems B2B sales professionals face? They're out of position from the moment they walk into a meeting. In this episode, Bill shares a tennis lesson that completely changed how he thinks about sales positioning, and reveals the three essential elements every salesperson needs to transform from a desperate "seller" into a trusted guide. You'll discover why most salespeople are closing only 15-20% of their deals (hint: prospects don't know what happens after they say "yes"), the simple roadmap strategy that doubled one company's close rate in 120 days, and how to position yourself as the obvious choice before you even have your first conversation. If you're tired of feeling like you're chasing prospects and want to start having them chase you, this episode will show you exactly how to make that shift. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com. 🎧 Ready to absorb these bold moves while on the go? Download the complete audiobook version at 12boldmoves.com/audiobook and transform your sales results during your commute, workout, or downtime.

    15 min

  5. AUG 7

    Why Prospects Lie to You (And How to Stop It)

    Ever wonder why prospects aren't being completely honest with you? In this episode, Bill reveals the uncomfortable truth: buyers think it's okay to lie to salespeople.  Drawing from 30 years in the business and insights from sales expert Terry Slattery, Bill explains why prospects withhold critical information and shares four proven strategies to inspire trustworthiness from the very first interaction. When you master these techniques, prospects stop looking for reasons NOT to work with you and start looking for reasons TO work with you. 12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

    11 min
  6. Stop Cold Calling Forever: How AI Can 3X Your Sales

    JUN 25

    Stop Cold Calling Forever: How AI Can 3X Your Sales

    Ready to transform your sales game? In this episode, Bill Caskey sits down with Jonathan Mast, founder of White Beard Strategies, to reveal how AI can revolutionize your sales process—without replacing you. If you're tired of endless cold calls, struggling to keep up with CRM updates, or feeling overwhelmed by your daily tasks, this conversation is a game-changer. Jonathan shares his journey from skeptical observer to AI advocate, explaining how he built a seven-figure business in under two years using AI as his secret weapon. Jonathan proves that AI isn't about working harder—it's about amplifying your existing skills to work smarter. Whether you want to work fewer hours for the same money or work the same hours to make 3-4x more, AI makes both possible. No tech background required—just a willingness to get in the game. This is part 1 of a special AI transformation series on the Bill Caskey Podcast. Stop going it alone—join our 2X Introductory Session and discover if you're one of the 10 people we'll accept this month: https://resources.billcaskey.com/2x-workshop 12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com. 🎧 Ready to absorb these bold moves while on the go? Download the complete audiobook version at 12boldmoves.com/audiobook and transform your sales results during your commute, workout, or downtime.

    27 min

  7. JUN 20

    5 Unpopular Sales Takes That Get Me Banned

    Why doesn't Bill get invited to traditional sales conferences anymore? In this no-holds-barred episode, he shares five controversial takes that challenge everything the sales industry has been teaching for decades. From why persuasion is overrated to why cold calling is a symptom of failed strategy, Bill dismantles conventional sales wisdom with brutal honesty. Warning: If you're deeply invested in traditional sales methods, this episode might make you uncomfortable. But if you're ready to challenge the status quo and build a modern revenue engine that actually works, this is your wake-up call. 2X Strategies Download: If you want to download all ten "2X Strategies", go here to get them now: https://billcaskey.com/2xstrategies 12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

    18 min

  8. MAY 22

    Turning Cold Calls Into Consulting Contracts: 5 Essential Steps

    In this episode, Bill shares a live coaching session with one of his clients - a leadership consultant who landed his first cold outreach call after just one week of working a LinkedIn strategy. Bill breaks down the exact 5-step framework he uses to help consultants and service providers turn initial prospect calls into profitable engagements. This episode is perfect for consultants, coaches, and service providers who want to scale beyond referrals and create a systematic approach to converting prospects into clients. He provides real-world examples and specific language you can use in your own sales conversations. 2X Strategies Download: If you want to download all ten "2X Strategies", go here to get them now: https://billcaskey.com/2xstrategies 12 Bold Moves: Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com. Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com. Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.

    12 min
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4.9
out of 5
25 Ratings

About

Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business.Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable insights and actionable advice that will help you build your skills and think differently about the profession of selling.Whether you're a seasoned sales professional or just starting out in your sales career, The Bill Caskey Podcast has something for you. So, join us every week as we explore the latest trends, techniques, and strategies for driving sales growth and success.To learn more about Bill Caskey and his work, visit www.billcaskey.com or follow him on LinkedIn at https://www.linkedin.com/in/billcaskey/.

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