The SellthatSaaS Podcast
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.
Episodes
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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...
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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...
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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...
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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!!!
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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...
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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…
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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…
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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…
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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…
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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...
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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...
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27: How TikTok Landed Me a Dream Sales Job
How can TikTok change your life? In this episode, I sit down with McKenna Johnson, a tech sales pro who used her TikTok content to land a dream job in sales at a cutting-edge AI company. We talk about breaking into SaaS, using content creation to book meetings, and how to leverage platforms like...
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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...
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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.
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24: Top learning lessons through starting a SaaS business from Jeff Hatten
I met Jeff Hatten on LinkedIn through his comedic & engaging content. This was the start of our friendship, however this episode you learn more about his story and how it led him to where he is today. Today Jeff resides in Colorado Springs, CO, and is the CEO of Popr.ai. Connect with Jeff here on...
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23: How Tech Jobs Unlock True Freedom
Want to break into tech sales and hit $100K while living life on your own terms? 💼 In this episode of the Sell That SaaS Podcast, I chop it up with returning guest Sharriff Dyer, a TikTok sensation with over 92K followers, as we dive into the blueprint for thriving in software sales. We talk…
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22: How Nick El-Tawil Thrives in Real Estate Sales
Ready for insider knowledge on "Real Estate Secrets for Sales Success 🚀"? On this episode of the Sell That SAS podcast, I talk with Nick El-Tawil, a fourth-generation Arizonan and real estate pro making waves in the Scottsdale market. We discuss everything from his journey starting in New York...
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21: Master the Art of Networking in Sales
Master the art of networking and building genuine connections without selling out! In this episode of the Sell That SaaS Podcast, I talk with Wulf Trigo, a business leader and expert in infinite banking, about how to approach networking, sell with empathy, and create lasting professional...
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20: Find the Mentor Who Will Transform Your Career
Looking to find the mentor who will transform your career? In this episode of the Sell That SAS podcast, I talk about the pivotal role mentorship has played in my journey through tech sales and content creation. From breaking into software sales as an SDR to navigating tough challenges as an AE…
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19: Christian Rapper Chvrch562 Talks about Using your Gift as of Discernment in the Workplace
This episode is a bit different, but in all the best ways. My friend Jerry Wright (Chrvch562) and I talk about our faith as a Christian, and using our gift of discernment in the workplace. #jesus #chrisitian #christianintech
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18: How to make your side hustle your full time hustle with Leslie Venetz
Ever wonder how to balance a side hustle with your corporate life? In this episode, I talk with Leslie Vanettes, a content creator with over 40K LinkedIn followers and 38K on TikTok, about breaking into tech sales, managing burnout, and leveraging social media for growth. We discuss her journey...
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17: How to grow your LinkedIn following with Zoë Hartsfield
In this episode of the "Sell That SaaS" podcast, I talk with LinkedIn influencer and Senior Manager of Evangelism at Apollo, Zoë Hartsfield, about how to monetize your LinkedIn and grow your personal brand. We discuss practical tips for breaking into content creation, building a LinkedIn…
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16: The Secret to Consistent Sales Success
Ready to sharpen your sales game? In this episode of the Sell That SaaS Podcast, I sit down with Mark Casaglow, former VP of Sales at Outreach, to break into his top SDR-AE secrets and career-defining strategies. From mastering cold calling with frameworks like "green turkey" to building…
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15: Vin Matano!!! - How to be your own Niche as a Content Creator
One of my best friends Vin Matano and I discuss all things New Jersey, New York, Katz Deli, and how to be your own niche when it comes to content creation on LinkedIn. In this episode of the Sell That SAS podcast, I talk with Vin Matano, aka @VinSellsTech, about how creators can break free from...
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14: Crush objections on the phone with EASE
In this episode of the Sell SaaS podcast, we talk about expert techniques for tough prospects in tech sales! I’m joined by Morgan Ingram, CEO of Amp, Tom Slocum, CEO of The SD Lab, and Sharriff Dyer, CEO of Wealth University, as we chop it up about overcoming objections, breaking into tech sales,...
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13: Master Influencer Marketing in Tech Sales with Scotty Scheller
In this episode of The Sell That Saas Podcast, I chop it up with my good friend and influencer marketing expert, Scotty Sheller. We talk about how to build authentic content, break into influencer campaigns, and effectively merge your passions with your career. Scotty shares his journey from...
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12: How to Level up in your sales career (From an Expert)
Unlock recruiter secrets to stand out in tech hiring for 2024! In this episode of the Sell That SaaS Podcast, I chop it up with recruiting legend Brent Orsuga, who’s placed over 1,000 candidates and has nearly 50K followers on LinkedIn. We talk about everything from breaking into tech sales to...
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11: Making a lifelong career in software sales
Learn to thrive as the first SaaS sales hire withAmanda Bagley ! In this episode of the Sell That SaaS podcast, I sit down with Amanda to talk about her journey from SDR to top-performing AE at startups like Chili Piper and Audience Plus. We discuss how to break into tech sales, navigate startup...
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10: The Secret to Breaking Into Tough Sales Jobs Fast
Ever wondered how to go from $66 to a six-figure income? In this episode of the Sell SaaS podcast, I talk with Jacob McLaughlin, who shares his inspiring journey from personal training to dominating the competitive world of medical device sales. We discuss how he broke into the industry, overcame...
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9: Why Every Sales Rep needs to Understand AI
In Episode 9 of the SellSS Podcast, we talk about why every sales rep needs to understand AI and how it’s shaping the future of tech sales. I’m back with Sharriff Dyer, a rising star in the tech space crushing it on TikTok with over 84K followers. We chop it up about the impact of AI on SDR…
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8: The Software Cowboy's Secret to 20X More Inbound Leads with Keegan Otter
Discover how The Software Cowboy generated 20X more inbound leads through authentic personal branding and strategic LinkedIn content. Join Will Padilla as he sits down with Keegan Otto, Head of Revenue at Warmly, who shares how his team grew from 10 to 240 inbound demo requests per month without...
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7: Avoid These COSTLY Mistakes in Your Tech Sales Career with Javier
Avoid costly mistakes that could derail your tech sales career! Join me as I chat with Javier Carrillo, former Inside Sales Director at Verkada and current Commercial Sales leader at Red Panda. We break down essential lessons learned from building successful sales teams and navigating career...
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6: The 3-Step Video Framework That Changed My Sales Career
Discover the 3-step video framework that transformed my sales career! In this episode, I break down my proven video prospecting strategy that generated 70% of my qualified meetings. Learn how to stand out in a crowded inbox and grab attention with personalized videos. I'll walk you through the...
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5: From SDR to AE in 10 Months: My Secret Playbook 🚀
Discover In this episode, I break down my exact blueprint for rapid promotion in tech sales. I talk about: • Why joining a startup can fast-track your career • The power of internal networking • My "Triple Threat" prospecting tactic that crushed quotas Learn how to stand out as an SDR and…
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4: The REAL Path to Tech Sales Success with Logan Little
Discover the REAL path to tech sales success with Logan Little, a veteran sales professional with over a decade of experience from door-to-door to software sales. In this value-packed episode, we dive into Logan's journey and uncover the strategies that actually work in today's competitive tech...
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3: The Psychology Behind 2X Cold Call Success with Morgan Ingram
Dive into the psychology of cold calling with sales expert Morgan Ingram! We break down his proven cold call opener that's led to 2X success rates and discuss why curiosity is crucial for SDRs. Morgan shares insights on: • The perfect cold call intro (and why it works psychologically) • How to...
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2 : How To Actually Land Your First Tech Sales Role with Sharriff Dyer
Breaking into tech sales? I chop it up with Sharriff, a TikTok sensation with over 84K followers, about insider secrets to launching your SaaS career. We discuss: • Sharriff's journey from real estate to tech sales • How to stand out in the competitive SDR job market • The pros and cons of remote...
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1: How Top SDRs Book More Meetings with Tom Slocum
Learn how top SDRs are booking more meetings in this chat with Tom Slocum, founder of SD Lab. We talk about the AE/BDR relationship, cold calling tactics, and the importance of phone outreach in tech sales. Tom shares his 16+ years of software sales experience and breaks down strategies for…
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About this 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.
Hosted by
Will Padilla
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