

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

Oct 18, 2021 • 12min
#672: Celebrating the small sales wins leads to the big ones with Kris Rudeegraap, Sendoso
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/

Oct 11, 2021 • 27min
#671: How can you stand out? with Kris Rudeegraap
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.

Oct 6, 2021 • 12min
Opinions vs Reality with Gong: Which CTAs book more meetings?
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

Oct 4, 2021 • 17min
#670: Getting Unstuck at the End
How do you get your deal unstuck when you’re nearing the end? In this episode, Bill and Bryan complete their three-part series on getting unstuck in the sales process. The guys address the end of the sales process when drama occurs and deals get stuck. They each give a few hints of how you can make this happen elegantly and organically with a minimum amount of drama. ========================================= 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 =========================================

Sep 29, 2021 • 14min
Opinions vs Reality with Gong: Selling with slides?
Should you use slides on a discovery call? Choose wisely because it impacts your chances of booking the next meeting by 17%. On this episode of Opinions vs. Reality, we are joined once again by Devin and Sheena from Reveal - the Revenue Intelligence Podcast. We give you our opinion on the impact of using slide decks. And, for when it’s the right decision, check out this cheat sheet for crafting sales decks that sell: https://pages.gong.io/crafting-sales-decks-checklist To listen to the Reality, subscribe to Reveal: The RI Podcast here: https://podcast.gong.io

Sep 27, 2021 • 21min
#669: Be Like Mike
How committed are you to personal growth? This episode was inspired by one of Bryan's clients, Mike, who has had a 30+ year career in sales but is still one of the most eager to learn ways and grow. The guys give you some ways you can be like Mike, and some way to stay motivated in your personal growth. ========================================= 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 =========================================

Sep 22, 2021 • 14min
Opinions vs Reality with Gong: I need to think about it
“I need to think about it” is the objection that makes every salesperson's skin crawl. But is it really the reason your deal didn’t close? In this special Opinions vs Reality, Bryan and Bill are joined once again by Devin and Sheena from Reveal: The Revenue Intelligence Podcast. Learn how to address any potential roadblock your seller might have. (Spoiler: It’s time to shift from sales to strategic advisor.) To listen to the Reality, subscribe to Reveal: The RI Podcast here: https://link.chtbl.com/i6UODNbY

Sep 20, 2021 • 20min
#668: Your Message Might Need Some Work
In this episode, Bill relays a story of one of his new clients who has asked for help on messaging. They sell a very complex solution to a large group of people in a long selling cycle. He is struggling with how to craft his message so that it’s compelling to the prospect. Bill and Bryan give you a handful of ideas on what to do and what not to do in this episode. ========================================= 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 =========================================

Sep 15, 2021 • 15min
Opinions vs Reality with Gong: Do you curse in sales?
Do you know the impact cursing has on your sales calls? In this special Opinions vs Reality episode, Bryan and Bill are joined by the hosts of Reveal: The Revenue Intelligence Podcast, Devin Reed and Sheena Badani. The guys give their best opinion on whether cursing hurts or helps the sale and then Devin and Sheena give them a hint on whether they are right. To listen to the Reality, subscribe to Reveal: The RI Podcast here: https://bit.ly/2VKDe6j

Sep 13, 2021 • 16min
#667: Stuck in the Middle With You
In this episode, Bill and Bryan talk about how to keep your sales process from getting stuck as you head into the center of it. This usually centers around people and processes not behaving properly. The guys give you some clues on what's going to help you navigate when you are stuck in the middle. ========================================= 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 =========================================