

The Advanced Selling Podcast
Bill Caskey and Bryan Neale: B2B Sales Trainers
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
Mentioned books

Nov 18, 2021 • 34min
The Best Sales Advice I Ever Received with John Barrows
Send us a text When you want great advice, you go to a great source. So, we went to one of the best. John Barrows built an empire based on his passion for sales. He believes sales is the greatest profession in the world when done right – and the worst when done wrong. In this episode, John gives us the best sales advice he's received in his career. Learn more about John at https://jbarrows.com. Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Nov 15, 2021 • 19min
#676: Is Sales Broken?
Send us a text Is sales really broken? In many ways it is. This episode was inspired by an email Bill received from Anthony Iannarino discussing why sales is broken. Anthony lists the stats that he's uncovered from both the seller and the buyer that backs up his belief. In this episode, Bill and Bryan start to break down the areas where they think sales is broken and they give you some ways you can reframe your thinking to accommodate the new ways of selling. ========================================= The Insider program is open for enrollment. If you have not checked out our version of a small learning group go to http://advancedsellingpodcast.com/insider to join today! Do you have a question you want to be answered on the podcast? Email us at listener@advancedsellingpodcast.com and we'll try to answer it on an upcoming episode! Looking for more sales training like this podcast? Download our FREE audio program, The Ultimate Pre-Game. http://ultimatepregame.com ========================================= Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Nov 11, 2021 • 10min
The Best Sales Advice I Ever Received with Mark Hunter
Send us a text In this exclusive series called "The Best Sales Advice I Ever Received," Bill and Bryan are handpicking some of the industry's top leaders to have them share the best advice that they've gotten in their careers. Sales legend, author, and speaker Mark Hunter joins Bill and Bryan in the studio this week with some simple yet profound advice: stay focused, stay consistent. These two foundational principles touch on every aspect of the sales process from your motivation level to your customer interactions to your learning. Tune in to this inspiring episode with the master “hunter” and guru of high-profit prospecting. To learn more about Mark, go to https://thesaleshunter.com. Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Nov 8, 2021 • 16min
#675: The Best Sales Advice Bill and Bryan Have Ever Received
Send us a text In this episode, Bill and Bryan kick off a series that they will be releasing throughout the weeks on The Best Sales Advice Ever — coming from authors and sales experts in our space. The guys thought there was no better way to kick it off than to have them share the best advice that they’ve received in their careers about sales and goal achievement. If you haven't already, go to advancedsellingpodcast.com/linkedin and join our group so that you can also weigh in on the best advice you’ve ever gotten on selling! ========================================= The Insider program is open for enrollment. If you have not checked out our version of a small learning group go to http://advancedsellingpodcast.com/insider to join today! Do you have a question you want to be answered on the podcast? Email us at listener@advancedsellingpodcast.com and we'll try to answer it on an upcoming episode! Looking for more sales training like this podcast? Download our FREE audio program, The Ultimate Pre-Game. http://ultimatepregame.com ========================================= Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Nov 1, 2021 • 12min
#674: How important is the customer experience when it comes to sales? with Kris Rudeegraap, Sendoso
Send us a text A business is made or slayed along the customer journey. Think US Airways. Blockbuster. When businesses fail, it’s usually due to a lack of empathy with their customers. Automated phone service, long wait times, Draconian return policies. The list goes on and on. The competitive advantage goes to companies who get it right. Think Apple. Wayfair. Trader Joe’s. You have to map out the customer’s journey and manage every single touchpoint along the way. For the salesperson, the customer experience doesn’t end when the deal is signed. The best salespeople keep coming around, maintaining that rapport over time. In this episode of The Advanced Selling Podcast, Kris Rudeegraap, CEO and Co-founder of Sendoso, shares his tips on enhancing the customer journey through empathy, energy, and generosity. He explains why account-based marketing (ABM) is like fishing with a spear instead of a fishing net. You won’t want to miss this one. AFTER YOU LISTEN: Check out the Sendoso platform and lunch is on the guys! https://sendoso.com/demo-request/ Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Oct 28, 2021 • 12min
The ASP 15 Year Anniversary!
Send us a text Celebrating 15 years of podcasts!! Bill and Bryan started the advanced selling podcast long before podcasting was a household word like it is today. Over those 15 years, the guys have recorded over 700 episodes. And have over 12 million downloads. We also honor all of those listeners who have been with us over the years, including those who started with us 15 years ago. Thank you! Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Oct 25, 2021 • 11min
#673: Gifting. Sales gimmick or great move? with Kris Rudeegraap, Sendoso
Send us a text You’ve heard the old saying… “Giving is better than receiving because giving starts the receiving process.” But does it work when it comes to sales prospecting? Absolutely. Studies show the ROI on gifting a prospect is high – and gifting a current client usually ends up in a longer-term relationship, repeat business, and more referrals. So… if you want to make an impact, differentiate, be remembered, and build goodwill, consider gifting. Spice up your prospecting efforts with creativity, thoughtfulness, and personalization. The key is to give without expectation. Whether it’s a welcome kit or free content – a podcast episode, a download, a handwritten note – it’s impossible to forget someone who’s gone out of their way to help. To learn more about the art of business gifting, check out the conversation with Kris Rudeegraap, CEO and Co-founder of Sendoso, the leading sending platform. AFTER YOU LISTEN: Check out the Sendoso platform and lunch is on the guys! https://sendoso.com/demo-request/ Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Oct 18, 2021 • 13min
#672: Celebrating the small sales wins leads to the big ones with Kris Rudeegraap, Sendoso
Send us a text For lack of a better cliché…sales is a rollercoaster. Highs. Lows. We’ve all been there. Building momentum is key. We’re usually so concerned with reaching the next peak that we forget to recognize the smaller wins along the way. And the worse culprits are oftentimes our managers This week, Kris Rudeegraap, CEO and CO-founder of Sendoso, the leading gifting platform, joins us to talk about putting the wind back in your sales, driving the momentum through the ups and downs – and why the proverbial pat on the back is critical. After you listen: Check out the Sendoso platform and lunch is on the guys! https://sendoso.com/demo-request/ Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Oct 11, 2021 • 27min
#671: How can you stand out? with Kris Rudeegraap
Send us a text We are not in the new normal - it's the next normal. Bill and Bryan believe that in this next normal, you have to humanize your brand. Kris Rudeegraap, CEO of Sendoso, joins the show for a special four-part series exploring innovative ideas to help you stand out. In this first episode, he shares how he went from SDR to tech founder, raising a $100 million Series C fund while highlighting one key tactic for creating differentiation. After you listen: BE SURE to register for a special live event focusing on trust How to build it, nurture it, and sustain it. Sendoso’s CONNECTED Conference is October 13 from 11am to 3pm (EST). And as an Advanced Selling podcast listener lunch is on Sendoso if you CLICK HERE and reserve your spot now! Join an all-star assembly of some of the best minds in marketing as they focus on TRUST, the key to better prospect and customer relationships, a better pipeline, and repeat business. It begins with credibility and ends when you stand out from the crowd. These 4 hours could change your business. Hosted by Trevor Noah, of The Daily Show, and Shola Richards, from Go Together Global. Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider

Oct 6, 2021 • 13min
Opinions vs Reality with Gong: Which CTAs book more meetings?
Send us a text After analyzing 300,000 cold emails, the team at Gong has debunked one of sales’ greatest mysteries — and unlocked a strategy to DOUBLE the amount of meetings you book. We are joined once again by the Devin and Sheena from Reveal: The Revenue Integillance Podcast. And, as you know, sales usually is not binary, typically nuances play into every situation. However, this is the exception. The CTA (call to action) you use at the end of your email, matters more than you think. To craft the perfect cold email, tune in to the episode then follow this link, https://pages.gong.io/highly-effective-email-ctas to find 43 emails proven highly effective by Gong’s research team. To listen to the Reality, subscribe to Reveal: The RI Podcast here: https://link.chtbl.com/i6UODNbY Join me December 5th for my Personal Business Planning Workshop where we'll build your complete 2026 blueprint in just two hours. Reserve your spot at advancedsellingpodcast.com/insider


