The SellthatSaaS Podcast

Hosted by Will Padilla

Business

Website RSS feed

Episodes

Latest episode

Aug 2026

Language

About the show

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.

Listen to episodes

37 recent

September 12, 2026Episode 3846 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. Takeaways Career 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. Chapters 00:00 Introduction and Common Faith 01:26 Career Journey in Tech Sales 03:05 Transition to Remote Work 04:07 Work-Life Balance and Promotion 05:01 Sales Skills and Approaches 07:24 Differences in Sales Environments 17:22 Sales Tactics and Demeanor 25:40 Understanding Different Personas 26:30 Dealing with Challenging Demos 28:14 Nuances of Sales Communication 31:19 The Importance of Volume in Sales 39:28 Ethical Conduct in Sales

August 13, 20261 hr 22 min

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 Stephen Lessons from leading at Microsoft Why relationships beat cold outreach How to build trust with prospects and customers What separates top salespeople from average reps Career success vs. success in life What Stephen wishes he knew earlier in his career

July 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.

June 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!!!

February 6, 20261 hr 1 min

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.

January 22, 2026Episode 331 hr 2 min

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/

December 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.

November 19, 2025Episode 3150 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

May 24, 202550 min

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

March 20, 202537 min

29: How Opinions Can Transform Your Sales Strategy

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 James got from marketing legend Seth Godin.Whether you're an SDR, AE, or content creator, this episode is packed with insights on pipeline generation, personal branding, and the future of sales. Don’t miss James’ hard-hitting takes and practical advice!#saas #techsales #sdr #ae #contentcreation #inboundsales #salesstrategyCHAPTERS:00:00 - Intro02:20 - Transition from Outbound to Inbound Marketing04:43 - Advantages of Content Marketing over Cold Calling07:44 - Major Deal Achieved through Content Strategy09:24 - Overcoming Fear of Judgment on LinkedIn12:24 - Coping with Client Loss Due to Content17:39 - Featured on LinkedIn Lunatics22:05 - Attack Campaign Strategies by Will28:31 - Tips for Individual Sales Representatives34:00 - Connecting with James Hamar35:19 - The Future of B2B Influencers37:20 - Subscribe for More Content