The SellthatSaaS Podcast

Will Padilla
  • 5.0 (5)
  • Business
  • Updated Biweekly

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.

  1. 1d ago

    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.

  2. Jun 5

    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!!!

  3. Feb 6

    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.

  4. Jan 22

    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/

  5. 12/03/2025

    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.

  6. 11/19/2025

    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

  7. 05/24/2025

    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

  8. 03/20/2025

    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

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About

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.

Information

  • Creator
    Will Padilla
  • Years Active
    2023 - 2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © Will Padilla
  • Show Website
    The SellthatSaaS Podcast