The SellthatSaaS Podcast

Doug Wood and I discuss his "WHY," in business and how it fuels him. We talk Faith, Marriage, Entrepreneurship, and sales. You're going to love this episode!!!

With AI exploding, layoffs making headlines, and SDR roles evolving fast, a lot of reps are asking the same question: should I stay in software sales… or pivot? In this episode of Sell That SaaS , I sit down with Dave McCarl — 20+ years in sales and over a decade in tech — to break down what’s actually happening in the industry. We talk AI vs human sellers, enterprise psychology, Latin America’s g...

I had one of my favorite conversations on the podcast with sales training expert Morgan Ingram. We get into what’s broken in sales training today, why coaching matters more than ever, and how top SaaS reps actually win deals. This episode is packed with real-world insight from someone who’s been in the trenches. Find Morgan on LinkedIn: https://www.linkedin.com/in/morganjingramamp/

Tom and I talk about leaving behind what others think you should do, and truly walk in your purpose for your career. Do you find yourself doing things just for the money? How about doing things because people told you it’s what you’re supposed to be doing? These are things that will keep you down. Work should feel like play, even on the days it feels like hard work.

On this episode of SellThatSaaS, host Will Padilla sits down with discovery & sales conversation expert Jonny Holsten (Bridge Selling) to fix the part of your process that’s quietly killing your deals: your discovery call. We unpack why most reps stop 2–3 questions too early, how to ask “why now?” without sounding pushy, the six categories every winning sales conversation hits, and how to stop adv...

Ready to unlock financial freedom? In this episode of the Sell That SAS podcast, I talk with Max Pashman, a certified financial planner with over a decade of experience helping sales leaders, content creators, and small business owners take control of their financial futures. Max breaks into expert tips on managing money, avoiding lifestyle creep, saving on taxes, and planning for long-term succes...

Why do inbound leads crush cold calls in the world of SaaS sales? 🚀 In this episode of the Sell SaaS Podcast, I chop it up with James H. Manolis, CEO of a content-led inbound agency and powerhouse in the B2B space. We talk about why inbound strategies outperform outbound cold calls, how content creation on platforms like LinkedIn and Twitter drives qualified leads, and the game-changing advice Ja...

In this episode of the Sell That SaaS podcast, I talk with Brandon Bornancin, CEO of seamless.ai, about how he scaled his company from zero to $200M in sales. We discuss breaking into tech sales, the power of side hustles, and the mindset it takes to dominate in SaaS. Brandon shares his entrepreneurial journey—from online poker to building a game-changing sales platform—and the lessons he learned...

In this episode, I chop it up with Keegan Otter, Head of Sales at Warmly, about building an unbeatable team culture in tech sales. We dive into how top sales leaders create a winning environment and the impact it has on performance. Keegan shares his secrets on leveraging LinkedIn for massive business growth - they've added nearly $1M in revenue just from their LinkedIn strategy! We also break dow...

Enterprise SaaS seller, Brandon Caldwell gives his story about how he went from prison, to sales. You'll love this episode. Connect with Brandon here, on LinkedIn.

I met Jeff Hatten on LinkedIn through his comedic & engaging content. This was the start of our friendship, however this episode you learn more about his story and how it led him to where he is today. Today Jeff resides in Colorado Springs, CO, and is the CEO of Popr.ai. Connect with Jeff here on LinkedIn. Thanks for watching!

Want to break into tech sales and hit $100K while living life on your own terms? 💼 In this episode of the Sell That SaaS Podcast, I chop it up with returning guest Sharriff Dyer, a TikTok sensation with over 92K followers, as we dive into the blueprint for thriving in software sales. We talk about how to go from zero experience to landing high-paying roles, the rise of the digital nomad lifestyle...

Ready for insider knowledge on "Real Estate Secrets for Sales Success 🚀"? On this episode of the Sell That SAS podcast, I talk with Nick El-Tawil, a fourth-generation Arizonan and real estate pro making waves in the Scottsdale market. We discuss everything from his journey starting in New York City real estate to dominating the ultra-competitive Arizona scene. Nick breaks into key strat...

Master the art of networking and building genuine connections without selling out! In this episode of the Sell That SaaS Podcast, I talk with Wulf Trigo, a business leader and expert in infinite banking, about how to approach networking, sell with empathy, and create lasting professional relationships. Wulf shares his journey from Spain to the U.S., overcoming challenges to build a thriving busine...

Looking to find the mentor who will transform your career? In this episode of the Sell That SAS podcast, I talk about the pivotal role mentorship has played in my journey through tech sales and content creation. From breaking into software sales as an SDR to navigating tough challenges as an AE, I share personal stories and practical tips to help you find the right mentor for your career. Whether...

This episode is a bit different, but in all the best ways. My friend Jerry Wright (Chrvch562) and I talk about our faith as a Christian, and using our gift of discernment in the workplace. #jesus #chrisitian #christianintech

Ever wonder how to balance a side hustle with your corporate life? In this episode, I talk with Leslie Vanettes, a content creator with over 40K LinkedIn followers and 38K on TikTok, about breaking into tech sales, managing burnout, and leveraging social media for growth. We discuss her journey from corporate sales leader to business owner, how to create a six-figure side hustle, and the value of...

In this episode of the "Sell That SaaS" podcast, I talk with LinkedIn influencer and Senior Manager of Evangelism at Apollo, Zoë Hartsfield, about how to monetize your LinkedIn and grow your personal brand. We discuss practical tips for breaking into content creation, building a LinkedIn following, and using social selling to drive results in tech sales. Zoë shares her journey from SDR t...

Ready to sharpen your sales game? In this episode of the Sell That SaaS Podcast, I sit down with Mark Casaglow, former VP of Sales at Outreach, to break into his top SDR-AE secrets and career-defining strategies. From mastering cold calling with frameworks like "green turkey" to building rock-solid SDR-AE partnerships, we cover it all. Mark also shares how he grew a massive LinkedIn audi...

One of my best friends Vin Matano and I discuss all things New Jersey, New York, Katz Deli, and how to be your own niche when it comes to content creation on LinkedIn. In this episode of the Sell That SAS podcast, I talk with Vin Matano, aka @VinSellsTech, about how creators can break free from their niche and build a unique personal brand. We discuss everything from breaking into tech sales, the...

In this episode of the Sell SaaS podcast, we talk about expert techniques for tough prospects in tech sales! I’m joined by Morgan Ingram, CEO of Amp, Tom Slocum, CEO of The SD Lab, and Sharriff Dyer, CEO of Wealth University, as we chop it up about overcoming objections, breaking into tech sales, and scaling your outbound strategies. We keep it real with actionable tips on standing out in today’s...

In this episode of The Sell That Saas Podcast, I chop it up with my good friend and influencer marketing expert, Scotty Sheller. We talk about how to build authentic content, break into influencer campaigns, and effectively merge your passions with your career. Scotty shares his journey from creating free content to landing massive brand partnerships with names like Cuts Clothing, Built, and Nike....

Unlock recruiter secrets to stand out in tech hiring for 2024! In this episode of the Sell That SaaS Podcast, I chop it up with recruiting legend Brent Orsuga, who’s placed over 1,000 candidates and has nearly 50K followers on LinkedIn. We talk about everything from breaking into tech sales to creating a killer personal brand that gets you noticed. Whether you’re an SDR, AE, or just starting out,...

Learn to thrive as the first SaaS sales hire with Amanda Bagley⁠ ! In this episode of the Sell That SaaS podcast, I sit down with Amanda to talk about her journey from SDR to top-performing AE at startups like Chili Piper and Audience Plus. We discuss how to break into tech sales, navigate startup life, and build a personal brand on platforms like LinkedIn. Amanda shares her take on thriving as a...

Ever wondered how to go from $66 to a six-figure income? In this episode of the Sell SaaS podcast, I talk with Jacob McLaughlin, who shares his inspiring journey from personal training to dominating the competitive world of medical device sales. We discuss how he broke into the industry, overcame constant rejection, and landed multiple job offers from top companies like Stryker and Medtronic—all w...