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The SellthatSaaS Podcast: Daily Summaries Delivered
by Will Padilla
The SellthatSaaS podcast is led by Will Padilla. The SellthatSaaS Podcast helps individuals break into tech, and also excel in their tech career once they have broken in. Will Padilla also has a strong interest in Faith and Financial wellbeing. Will has over 40,000 followers across LinkedIn, TikTok, YouTube, and Instagram.
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- 1 weeks ago46 min
Episode 38- Trust Jesus & Work Hard, Anthony Calabrese
The conversation begins with an introduction and a discussion about common faith, leading into a detailed exploration of the guest's career journey in tech sales. The transition to remote work, work-life balance, and promotion are then discussed, followed by an exploration of sales skills and approaches. The conversation delves into differences in sales environments, sales tactics, and demeanor. The conversation delves into the nuances of sales communication, the importance of understanding different personas, and the ethical conduct in sales. It also explores the challenges of dealing with difficult demos and emphasizes the significance of volume in sales.TakeawaysCareer growth in tech sales requires a strong work ethic and a focus on high-volume activities.Sales skills and approaches vary based on the sales environment and the nature of the interaction with prospects. Understanding different personas is crucial in sales communication.Ethical conduct and prioritizing value over volume are essential in sales.Chapters00:00 Introduction and Common Faith01:26 Career Journey in Tech Sales03:05 Transition to Remote Work04:07 Work-Life Balance and Promotion05:01 Sales Skills and Approaches07:24 Differences in Sales Environments17:22 Sales Tactics and Demeanor25:40 Understanding Different Personas26:30 Dealing with Challenging Demos28:14 Nuances of Sales Communication31:19 The Importance of Volume in Sales39:28 Ethical Conduct in Sales
- Aug 13, 20261h 22m
37 - Top Sales & Life Lessons from Stephen Oommen
In Episode 37 of the SellThatSaaS Podcast, I sit down with Stephen Oommen, CEO of the Referral Effect, who is a former Microsoft sales executive with more than 25 years of experience in sales and leadership.This conversation goes way beyond hitting quota.Stephen shares the biggest lessons he's learned throughout his career, from building relationships and earning trust to redefining what success actually means. We talk about what separates great salespeople from everyone else, why your network matters more than ever, and the lessons about life that become clearer after decades of chasing success.If you're in sales, building a career, or trying to figure out what actually matters along the way, this episode is for you.In this episode:What 25+ years in sales taught StephenLessons from leading at MicrosoftWhy relationships beat cold outreachHow to build trust with prospects and customersWhat separates top salespeople from average repsCareer success vs. success in lifeWhat Stephen wishes he knew earlier in his career
- Jul 29, 202643 min
Episode 36: You Cannot Generate Revenue without Pipeline - Sean Tatarian
Sean was my BDR manager during my first software sales role, and someone I look to as a mentor. Sean is by far, the most intelligent and kind BDR leader I have ever met. Connect with Sean here, https://www.linkedin.com/in/sean-tatarian/He has over 10 years of SDR Leadership experience, enjoy the episode.
- Jun 5, 202656 min
Episode 35 - Doug Wood - CEO of Hive Fit Club in Scottsdale, AZ
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!!!
- Feb 6, 20261h 1m
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.
- Jan 22, 20261h 2m
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/
- Dec 3, 202542 min
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.
- Nov 19, 202550 min
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
About The SellthatSaaS Podcast
The SellthatSaaS podcast is led by Will Padilla. The SellthatSaaS Podcast helps individuals break into tech, and also excel in their tech career once they have broken in. Will Padilla also has a strong interest in Faith and Financial wellbeing. Will has over 40,000 followers across LinkedIn, TikTok, YouTube, and Instagram.
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