The SellthatSaaS Podcast

34: Is Tech Sales Still Worth It?

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 growing tech opportunity, partnerships, career intentionality, and why being a “Swiss Army Knife” rep might be your unfair advantage. If you’re an SDR, AE, or thinking about breaking into tech sales, this is the real conversation.

33: What Actually Works in SaaS Sales

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/

32: Joy Over Revenue - with Tom Slocum

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.

31: You're Losing Deals in Discovery (Here's Why)

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 advancing bad-fit inbound leads that clog your pipeline. We get into outbound vs inbound strategy, how to qualify with integrity, what to do when a prospect “has no timeline,” and why pain + timing matter more than any fancy demo you’ll ever run.If you’re tired of “let me think about it” endings, ghosted follow-ups, and marketing asking why you didn’t close a “good” lead, this episode will give you real frameworks, real language, and a new way to run discovery that actually closes.👉 Connect with Jonny: bridgeselling.com & “Fix Your Broken Sales Calls”👉 Connect with Will on LinkedIn: https://www.linkedin.com/in/william-padilla/👉 Subscribe for more SaaS sales, faith & career episodes every week.00:00 – Welcome Back to the Podcast01:10 – Why Will Took a Break (Life + Wedding Updates)02:20 – Introducing Jonny Holsten04:00 – Jonny’s Background: Marketing → Sales07:00 – What Bridge Selling Actually Does10:00 – The 6 Parts of a Winning Discovery Call13:20 – When Buyers Take Control of the Call16:00 – Inbound vs Outbound (Why They’re Totally Different)19:00 – The #1 Question Great Reps Always Ask22:00 – The Power of Slowing Down in Sales25:00 – Why Good Reps Don’t Assume27:20 – The Biggest Mistakes Reps Make in Discovery30:15 – Feature Dumping vs Connecting to Pain33:40 – “We’re Not a Fit for Everyone” (How to Take Control)36:50 – What Happens When There’s No Pain40:00 – How Marketing & Sales Misalign on Lead Quality43:20 – What To Do When Buyers Have “No Timeline”46:20 – Creating Real Urgency Without Manipulation49:00 – Final Takeaways: Mastering Discovery for SaaS50:15 – Where to Find Johnny + Book Info51:00 – Closing Thoughts & Next Episode Preview

30: Unlock Financial Freedom with These Expert Tips

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 success. Whether you're in tech sales, content creation, or running your own business, these actionable insights will help you build wealth and set yourself up for success. We discuss everything from maximizing your savings rate to the importance of time in the market, plus common financial mistakes to avoid in your 20s and 30s. Max also shares how modern tools like LinkedIn transformed his career and allowed him to create a client-focused, holistic approach to financial planning. If you're looking to grow your income, save smarter, and achieve your goals, this episode is packed with value. Don’t miss out on this relatable, practical advice for creating a secure financial future! 🙌 #saas #techsales #sdr #ae #financialfreedom #entrepreneurship #sidehustle #contentcreation #moneytips CHAPTERS: 00:00 - Intro 03:18 - The Power of LinkedIn for Networking 09:14 - What Makes Max Unique as a Financial Advisor 10:40 - Strategies for Getting Introduced to Influential People 13:41 - Common Mistakes in Your Late 20s and Early 30s 17:31 - Importance of Time in the Market for Investments 24:05 - Understanding Lifestyle Creep and Its Impact 28:26 - Strategies to Address and Manage Lifestyle Creep 30:57 - Reasons Why People Avoid Investing 34:38 - Feeling Like Life Happens Too Fast: Insights 38:19 - The Real Cost of College Education 39:08 - 3 Legal Tax Savings Strategies for Small Business Owners 42:10 - Essential Financial Advice for People in Their 20s 44:06 - Top Financial Mistakes to Avoid in Your 20s and 30s 47:54 - How to Connect with Max Pashman 49:28 - The Importance of Financial Freedom 49:40 - Closing Remarks