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!!!
Episodes
34
Latest episode
Jun 2026
Language
EN
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
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 #moneytipsCHAPTERS:00:00 - Intro03:18 - The Power of LinkedIn for Networking09:14 - What Makes Max Unique as a Financial Advisor10:40 - Strategies for Getting Introduced to Influential People13:41 - Common Mistakes in Your Late 20s and Early 30s17:31 - Importance of Time in the Market for Investments24:05 - Understanding Lifestyle Creep and Its Impact28:26 - Strategies to Address and Manage Lifestyle Creep30:57 - Reasons Why People Avoid Investing34:38 - Feeling Like Life Happens Too Fast: Insights38:19 - The Real Cost of College Education39:08 - 3 Legal Tax Savings Strategies for Small Business Owners42:10 - Essential Financial Advice for People in Their 20s44:06 - Top Financial Mistakes to Avoid in Your 20s and 30s47:54 - How to Connect with Max Pashman49:28 - The Importance of Financial Freedom49:40 - 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
February 12, 2025Episode 2845 min
28: From Side Hustle to SaaS Empire
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 along the way. Tune in for insights on scaling your business, crushing your sales goals, and leading with purpose. #saas #techsales #sdr #ae#coldemail #techsales #leadgeneration #b2bmarketing #saassalesCHAPTERS:00:00 - Intro00:50 - Brandon, CEO of Seamless.ai05:00 - InMobile Overview06:30 - Bankruptcy Insights08:20 - Getting Fired Experience10:30 - Getting Into Sales Tips14:57 - Seamless.ai Overview19:20 - Going Full-Time with Seamless24:08 - Finding True Happiness26:30 - Money and Time Freedom31:50 - Breaking into Tech Sales33:55 - Essential Sales Tools34:59 - A Day in Brandon's Life42:33 - Health and Success Connection44:28 - Connecting with Brandon
January 8, 202556 min
26: How Top Sales Leaders Build Unbeatable Team Culture with Keegan Otter
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 down: • The importance of community in sales success • How to talk about competitors without mudslinging • Practical tips for sales leaders to foster trust and accountability Whether you're an SDR, AE, or sales leader, this episode is packed with actionable insights to level up your tech sales game. Keegan drops some serious knowledge on how Warmly has grown from 15 to 50+ employees and increased ACV by 50% with smart leadership tactics. #techsales #salesleadership #linkedin #saas #competitiveselling Don't miss this value-packed conversation on building high-performing sales teams and crushing your quotas! #onlinecommunity #howtoimproveteamcultureatwork #improveyourculture #talentacquisition #softskills CHAPTERS: 00:00 - Intro 01:03 - Keegan Otter’s Introduction 06:57 - Importance of Leadership in Sales 18:15 - Community Impact for Sales Reps 21:40 - Managing Top Performers and Process Compliance 31:30 - Warmly's LinkedIn Strategy for $1M ARR Growth 34:50 - SDRs and LinkedIn Posting Requirements 38:58 - Strategies for Discussing Competitors 47:40 - Winning Deals Against Competitors 49:10 - Anti-Selling Techniques 54:55 - Finding Keenan Online 55:47 - Outro
December 4, 202444 min
25: How traumatic life experiences can give you the ability to relate to others, Brandon Caldwell
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.
Is this your show?
Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.
Claim this listing
