The SellthatSaaS Podcast

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.

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/

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.

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

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

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

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

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 TikTok and LinkedIn to build your personal brand. McKenna shares her journey from teaching to crushing it in tech sales, her tips on using social media to connect with decision-makers, and the story behind how one viral TikTok opened doors to her dream role. If you're curious about how to excel in tech sales, grow your online presence, or land your dream sales job, this episode is packed with actionable advice. Whether you're an SDR, AE, or just starting out, there's something here for everyone. #saas #techsales #sdr #ae #contentcreation #personalbranding #tiktokmarketing #salescareers #linkedinsalesnavigator #tiktokadstutorial #leadgeneration #tiktokbusinessaccount #contentmarketing CHAPTERS: 00:00 - Intro 04:00 - Journey into Sales 07:47 - Walter and AISRD Overview 11:17 - McKenna's SalesLoft Journey 15:22 - First Day at SalesLoft 18:35 - McKenna's Job Departure 26:15 - Women in Male-Dominated Offices 27:44 - Creative Storytelling 32:41 - Introvert Experiences 33:58 - Importance of Activity 37:35 - Super Cities Concept 41:34 - YouTube Transition 45:13 - LinkedIn Strategies 45:37 - Content Planning Tips 48:27 - YouTube Transition Insights 52:20 - Ideal Partnerships 54:43 - Connect with McKenna Elizabeth 55:40 - Upcoming Episode Teaser 56:13 - Outro

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

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.

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 LinkedIn.Thanks for watching!

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 about how to go from zero experience to landing high-paying roles, the rise of the digital nomad lifestyle, and how living abroad can stretch your earnings to millionaire levels. 🌴We also discuss the power of content creation, the importance of collaboration, and how to leverage skills like sales and negotiation to create financial freedom. Sharriff shares real success stories from his community, including people who’ve turned their lives around in just 30 days! Whether you’re in tech or looking for motivation to start your next chapter, this conversation is packed with value.#saas #techsales #sdr #contentcreation #digitalnomad #salescareer #remotework #financialfreedom #softwarejobsCHAPTERS:00:00 - Intro01:15 - What's New with Sharriff03:16 - Content Collaboration Strategies04:28 - Digital Nomad Experience07:20 - The Lie of the Matrix Explained09:42 - How to Escape a Bad Job14:07 - Understanding Inflation18:11 - Printing Money Out of Thin Air22:44 - Living in America Long Term24:38 - Importance of Location Flexibility26:39 - Future Goals and Aspirations29:35 - Episode Wrap-Up30:50 - God's Timing is Perfect34:00 - Giving Glory to God35:35 - How to Connect with Sharriff

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 City real estate to dominating the ultra-competitive Arizona scene. Nick breaks into key strategies for building a standout real estate career, navigating market shifts, and leveraging content creation on platforms like Instagram to drive leads.We also talk about Arizona's unique real estate trends, how buyers and sellers can win in today’s market, and Nick’s expert tips for staying consistent in a tough industry. Whether you're in real estate, tech sales, or just looking for inspiration, there’s practical advice here for everyone chasing success. #realestate #salessecrets #contentcreation #arizonarealestate #techsales #saas #sdr #aeCHAPTERS:00:00 - Intro01:03 - Nick El-Tawil Introduction03:10 - Baruch College Experience07:35 - Working with Ryan Serhant09:50 - Impact of Content on Real Estate Career10:40 - Considering a Side Job13:30 - Typical Day in Real Estate14:45 - Arizona Real Estate Market Overview15:55 - Trends in In-State Moving to Arizona18:14 - Current Events in Arizona Real Estate21:53 - Agent Matt's Specialization22:52 - Overview of Real Estate Market Trends24:45 - Matt's Favorite Arizona Spot27:35 - Advice for Real Estate Professionals30:32 - Recent Changes in Real Estate Law33:56 - Carvana's Impact on Market35:44 - Where to Find Nick El-Tawil36:39 - Outro

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 relationships. Wulf shares his journey from Spain to the U.S., overcoming challenges to build a thriving business, and breaks down practical tips for connecting with highle individuals without being pushy.#saas #techsales #networkingtips #sdr #ae #businessgrowth #salesstrategyCHAPTERS:00:00 - Intro02:33 - Wulf's Background08:37 - Starting a Roofing Business11:25 - Car Curse18:49 - Why Arizona is the Best State21:18 - Why California is the Worst State23:25 - The Supercar Effect Explained27:35 - Wealthy Mindsets: Beyond Flashy Items30:33 - Navigating Wealthy Circles38:58 - Effective Networking Strategies40:38 - Importance of Getting Out There43:04 - Networking Like a Pro46:00 - Asking vs Active Listening in Networking51:00 - Tips for Getting on Stage51:50 - Mastering In-Person Sales Techniques53:52 - Connecting with Wulf56:16 - Final Thoughts and Insights

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, I share personal stories and practical tips to help you find the right mentor for your career. Whether it’s overcoming obstacles, excelling in your role, or planning your next big move, having someone in your corner can make all the difference. Plus, I discuss how to connect with mentors online and in person, the value of humility in learning, and why mentorship is key to long-term success in this cutthroat industry.If you’re in software sales—or thinking about breaking into it—this is the real talk you need to hear. Let’s explore how mentorship can guide you to new heights! #saas #techsales #sdr #ae #mentorship #careergoals #contentcreationCHAPTERS:00:00 - Intro01:48 - How to Find a Mentor05:39 - Career Mentorship Strategies10:48 - The Impact of Mentorship18:00 - Importance of Mentorship19:00 - Value of Wise Advisors20:50 - Learning from Older Generations21:40 - Collaborative Journey in Mentorship22:10 - Seeking Guidance from God22:55 - Final Tips and Reminders23:55 - Leave A Review

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

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 from corporate sales leader to business owner, how to create a six-figure side hustle, and the value of staying authentic on TikTok and LinkedIn. Whether you're thinking about starting a side hustle, breaking into SaaS, or just looking for tips to manage your time better, this one's for you!

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 following, and using social selling to drive results in tech sales. Zoë shares her journey from SDR to marketing leader, her secrets for landing brand deals, and how she balances a full-time SaaS career with thriving influencer partnerships.Whether you're in tech sales, looking to grow your side hustle, or just curious about content creation, this episode is packed with actionable insights and relatable advice. Learn how to target the right audience, create engaging content, and start monetizing your LinkedIn presence like a pro.Don’t miss out on Zoë’s expert tips and real-world examples to help you level up your LinkedIn game and unlock new opportunities in your career.#saas #techsales #sdr #ae #contentcreator #personalbranding #socialselling #b2bmarketing #socialselling #leadgeneration #linkedinleadgeneration #b2bmarketing #linkedinmarketingCHAPTERS:00:00 - Intro01:10 - Zoë Hartsfield Introduction06:00 - Future of Remote Work09:28 - Building Personal Brand Full-Time12:24 - Journey into Content Creation16:40 - Writing Effective Hooks23:17 - Social Selling Strategies25:05 - LinkedIn for Brand Partnerships30:20 - Securing Brand Deals with Will33:44 - Choosing Brand Partners35:14 - Disqualifying Partnerships Early37:10 - Replacing Low-Paying Partnerships38:43 - Inbound Meetings through Social Selling40:48 - Starting Small and Growing43:18 - First Brand Deals Experience46:15 - Dealing with Online Hate49:04 - Spending Money Wisely54:31 - Finding Zoë HartsfieldConnect with Zoë here on LinkedIn and send her a message that you found her episode on the SellthatSaaS podcast helpful!

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 rock-solid SDR-AE partnerships, we cover it all. Mark also shares how he grew a massive LinkedIn audience of 51K by staying authentic and consistent. We talk about how to excel in tech sales, maintain accountability with nonnegotiables, and stand out in your company. Plus, Mark opens up about his journey scaling Outreach from zero to $250M and the lessons he learned from the best go-to-market minds. Whether you're an SDR or AE looking to level up, this episode is packed with practical tips you can use today.#saas #techsales #sdr #ae #salesstrategy #contentcreation #salesleadership #linkedinstrategy#leadgeneration #techsales #salesdevelopmentrepresentative #b2bsales #saassalesCHAPTERS:00:00 - Intro01:15 - How Will and Mark Met03:49 - Mark's LinkedIn Presence08:51 - Mark's Involvement with 30MPC09:56 - Mastering Effective Sales Techniques13:14 - Value of a Cold Calling Script14:56 - Will’s Flexible Framework for Cold Calling18:06 - The Green Turkey Technique Explained18:58 - The 3 Strikes You're Out Technique21:07 - Keys to Sales Success23:44 - Understanding the Sine Wave of Sales26:37 - Full-Cycle AEs: Pros and Cons31:56 - The Future of SDRs35:50 - Running an Effective SDR Team39:40 - Benefits of Parallel Dialers43:00 - Favorite Aspects of Sales44:54 - Addressing "Unsexy" Products in Sales49:44 - Connecting with Mark49:53 - Essential Traits for Salespeople51:10 - Sam’s Recap of the EpisodeConnect with Mark here on LinkedIn! Tell him that you heard him on the SellthatSaaS podcast as well!

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 their niche and build a unique personal brand. We discuss everything from breaking into tech sales, the rise of B2B influencer marketing, and practical ways to monetize your content. Vin, a six-year veteran in tech sales and a successful content creator, shares insights on balancing life as a creator, navigating brand partnerships, and why it’s important to showcase your personality outside of your career. #SaaS #TechSales #SDR #AE #ContentCreation #B2BMarketing #PersonalBranding #InfluencerMarketingCHAPTERS:00:00 - Intro02:35 - Insights from Twine Product Advisory Meeting05:10 - Vin's Lifestyle on Social Media09:20 - Monetization Strategies for Creators11:05 - How to Monetize as a Creator14:00 - Text Creators vs Video Creators17:10 - Will and Jack’s High School News Show19:28 - Content Creation Earning Potential20:25 - B2B Influencer Marketing Overview21:37 - Future Trends in LinkedIn22:38 - Understanding No-Click Content23:35 - Tracking Attribution in Marketing25:18 - Influencer Marketing Experiments26:48 - Final Thoughts32:30 - Embracing a Nicheless Approach35:49 - Connecting with Vin36:43 - OutroConnect with Vin here on LinkedIn!Vin has over 18k Followers on TikTok, 23k on LinkedIn, 5k on YouTube, and 40k on Instagram. Talk about star studded!!

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, and scaling your outbound strategies. We keep it real with actionable tips on standing out in today’s job market, using personalization at scale, and crafting Loom videos to close deals. We also dive into the power of LinkedIn, building a content creation strategy, and practical advice for sales pros moving from SDR to AE roles. Whether you're hitting quota or trying to break into the industry, this episode is packed with gems to level up your game. #saas #techsales #sdr #ae #contentcreation #salesstrategy #careergoals#techsales #salesdevelopmentrepresentative #b2bsales #saassales #softwaresalesCHAPTERS:00:00 - Intro02:54 - Job Market Strategies04:47 - Job Market Insights (Sharif)09:47 - Job Acquisition Techniques12:21 - Job Acquisition Techniques (Continued)19:14 - Importance of Personal Branding22:09 - Internal vs External Branding24:56 - Benefits of Branding26:15 - Encouraging Brand Building28:14 - Social Media Posting Tips30:29 - Skills Assessment32:55 - LinkedIn Influence33:53 - The Wheel of Fun34:20 - Effective Cold Email Subject Lines34:25 - Selling Techniques: Glass of Water34:29 - Overcoming "I Need to Think"41:25 - Roleplay Session47:05 - Finding Your Unique Style51:30 - Tom’s Cold Call Analysis56:03 - Debriefing Session56:15 - Improving Call Techniques59:07 - Addressing Relevant Use Cases1:01:06 - Roleplay Exercise1:07:54 - Feedback Session1:13:26 - Rapid Fire Questions1:15:37 - Cold Call Openers1:21:50 - Building Rapport1:24:21 - Follow-Up Timing Strategies1:24:50 - Conclusion1:25:27 - Guest InformationIf you enjoyed this episode, please consider purchasing my 0-100 Cold Call guide to ace your cold calls with ease. Lastly, if you found this episode entertaining, helpful, etc. please message me directly if you want more of this type of podcast. I am blessed that all three of the guests live in Scottsdale alongside me.

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 creating free content to landing massive brand partnerships with names like Cuts Clothing, Built, and Nike. We also discuss: - How to balance content creation with a 9-to-5. - Why authenticity is key in influencer marketing. - Tips for scaling your tech sales career through creative strategies. - Real monetization techniques for creators. Whether you're in SaaS, software sales, or just want to learn how to grow your brand, this episode is packed with insights you can’t afford to miss. #saas #techsales #sdr #ae #influencermarketing #contentcreation #growthmindset #performancemarketing #emailmarketing #digitalmarketing #influencermarketing #leadgenerationCHAPTERS:00:00 - Intro01:10 - Scotty's Current Projects05:18 - Monetizing Your Influence13:02 - Stepping Out in Faith16:25 - Starting with Free Content19:45 - B2B Influencer Marketing Gaps22:14 - Evaluating Brand Deals23:56 - Value of Testimonials in Marketing29:05 - Managing Multiple Brand Deals32:50 - Securing Big Brand Partnerships37:08 - Understanding Influencer Contracts39:40 - Best Clothing Brands for Influencers41:25 - Measuring Success as an Influencer45:56 - Breaking the Paycheck Cycle51:14 - Defining Your Financial Goals53:37 - Using Money to Generate More Income55:30 - Starting Without Expensive Equipment57:14 - Networking with Successful Individuals1:00:20 - Earning Potential as a Micro-Influencer1:03:06 - Investing in Yourself1:03:58 - Connecting with Scotty1:05:48 - OutroScotty is a major brand influencer for brands such as Bylt Basics, Tomahawk Shades, Manscaped, and many others. Lastly, the SellthatSaaS podcast also just released our first cold calling guide that will help you crush it on the phones. Get yours here!

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 creating a killer personal brand that gets you noticed. Whether you’re an SDR, AE, or just starting out, this episode is packed with tactical insights to help you crush your goals and thrive in tech sales. Don’t miss this conversation for actionable advice to take your career to the next level! #saas #techsales #sdr #ae #careeradvice #recruitingtips #personalbranding #jobsearchtips #techsales #accountexecutive #breakingintosoftwaresales #talentacquisition #businessdevelopmentCHAPTERS:00:00 - Intro00:50 - Brent's Background02:35 - Career Change Strategies04:28 - Enhancing Candidate Experience05:27 - Benefits of Working with a Recruiter06:38 - Candidate Awareness Tips08:15 - Social Media's Impact on Job Search12:18 - Job vs Career: Key Differences13:11 - Promotion and Salary Insights17:20 - Influence of Your Circle21:50 - Fitness and Career Success25:27 - Networking and Career Impact27:36 - Handling Intensity Perceptions31:28 - Strategies to Stand Out32:00 - Coping with Layoffs33:34 - Connecting with BrentConnect with Brent here on LinkedIn.

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 life, and build a personal brand on platforms like LinkedIn. Amanda shares her take on thriving as a woman in tech, balancing the hustle, and leveraging owned media for sales success. If you're looking for practical advice on making an impact in SaaS sales, this one’s for you!#saas #techsales #startuplife #contentcreation #sdr #ae #womenintech #salescareer #linkedinstrategy #techsales #saas #softwaresales #accountexecutive #howtohiresalespeopleCHAPTERS:00:00 - Intro01:48 - Amanda’s Career Journey in Sales06:32 - Being a Woman in Sales: Challenges and Insights12:05 - Why Startups are the Best for Sales Careers17:54 - Amanda as a Sales Promoter18:46 - Understanding Owned Media in Sales22:15 - Exploring Audience Plus for Sales Growth24:50 - Why Content Teams Will Win in Sales27:30 - Amanda’s Content Journey in Sales30:50 - The Future of Amanda’s Career34:00 - Navigating Tech Layoffs in Sales34:39 - What to Do When You Get Laid Off38:15 - Living in Arizona: Amanda’s Experience39:14 - Building a Sales Community: Importance and Strategies41:02 - Outbound Strategies for Audience Plus47:41 - Key Takeaways and Missed Points53:50 - Where to Find Amanda Online55:11 - Outro

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 constant rejection, and landed multiple job offers from top companies like Stryker and Medtronic—all without traditional sales experience. Whether you're looking to crush it in tech sales, medical sales, or just need some motivation to level up, this conversation is packed with actionable insights and inspiration. Don’t miss Jacob’s advice on using rejection as fuel and how to stand out in ultra-competitive industries. #saas #techsales #medicaldevicesales #contentcreation #sdr #ae #salesstrategy #careersuccess #salesmotivation CHAPTERS: 00:00 - Intro 01:24 - Jacob’s Journey to Medical Device Sales 05:16 - Overcoming Odds in Medical Device Sales 08:49 - Doing the Job to Get the Job 11:27 - Reality of Today's Job Market 14:36 - Job Market Challenges 15:31 - Every Day, Rent is Due 16:40 - How to Get Hired in Medical Sales 19:20 - Getting Hired (Continued) 21:50 - Meaningful Gestures in Networking 27:40 - Transitioning to Medical Sales Careers 30:08 - Role of a Great Mentor 32:00 - Importance of Content in Sales 35:00 - Giving Advice with Less Experience 38:36 - Defining Your Haters 40:38 - Value in Medical Device Sales 44:29 - Fill Your Cup: Self-Care Tips 45:07 - Jacob's Success Through Faith 49:14 - Gaining the World vs. Losing Your Soul 52:27 - Loving the Process of Growth 57:50 - Power of Content in Sales 58:25 - Where to Find Jacob Follow Jacob here on LinkedIn.

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 roles, how top reps can leverage tools like ChatGPT and SendSpark, and practical ways to stay ahead in an evolving sales landscape. We also break down: - Tips to break into tech sales and stand out in competitive interviews. - How AI tools can help SDRs and AEs personalize outreach, practice cold calls, and boost productivity. - Why time management and setting boundaries are critical for success. - The role of content creation in building a personal brand and opening doors in tech. Whether you're an SDR, an AE, or just looking to level up your sales game, this episode is packed with actionable insights. Don't miss Sharif’s take on combining AI and sales strategies to stay at the top. #saas #techsales #ai #sdr #ae #salesrep #contentcreation #softwarejobs #careergoals #aiautomationagency #techsales #leadgeneration #sdr #makemoneywithai CHAPTERS: 00:00 - Intro 01:55 - AI Impact on SDR Role 05:17 - AI Sales Techniques 06:41 - Understanding AI for SDRs 10:25 - Necessity of AI in Tech Companies 12:45 - The Future of Remote Work 17:04 - Challenges of Hustle Culture 18:17 - Gen Z Perspectives on Work 19:50 - Is $100k Enough in America? 23:47 - Understanding Take-Home Pay 26:47 - Buying My First Condo at 20 29:54 - Homeownership Accessibility 33:48 - Physical vs Digital Currency 36:20 - Reasons for Booking Time Today 37:50 - ROI of a $100 Investment 45:06 - Our Offerings Explained 48:50 - Final Thoughts and Insights 56:20 - Advice for SDRs 59:10 - Outro

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 spending on ads. Learn how personal branding is transforming B2B sales and why LinkedIn has become their #2 source of qualified leads. Keegan breaks down his journey from SDR to executive leadership by age 27, sharing tactical advice for sales professionals looking to accelerate their careers. Key topics covered: • How to build an authentic personal brand that drives inbound leads • Transitioning from cold outbound to warm inbound strategies • Leveraging video content and multi-channel approaches • Building and scaling high-performing sales teams • The future of AI in sales prospecting Perfect for SDRs, AEs, and sales leaders looking to generate more inbound opportunities through personal branding and modern sales techniques. #SaaS #TechSales #PersonalBranding #B2BSales #SalesLeadership #InboundLeads #linkedinsalesnavigator #saas #leadgeneration #linkedinoutreach #saasmarketing CHAPTERS: 00:00 - Intro 01:09 - Keegan’s Sales Journey 04:48 - How Keegan Got to Scottsdale 12:40 - Excel in Sales Role 13:49 - Transition to Leadership 17:24 - Software Tools for Sales Success 19:55 - Rate of Change in Sales 21:56 - Age and Software Sales 26:17 - Building Your Personal Brand 30:11 - Future of B2B Influencer Marketing 32:42 - Personal Brand and Inbound Leads 37:02 - Warmly's Inbound Success 39:52 - Importance of Authenticity 41:21 - Senspark Overview 45:18 - Connect with Keegan 49:44 - Outro 50:00 - Finding Keegan 50:15 - Final Thoughts Connect with him here.

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 transitions in tech. Javier shares raw insights from his journey through Samsara, Verkada, and Glen Coco, including why he left high-growth companies and what he learned along the way. We discuss the evolution of remote work, building genuine relationships in sales, and how to know when it's time to make a career move. Get insider perspective on: - Making strategic career decisions in tech sales - Building valuable professional networks - Balancing personal brand with sales performance - Why Scottsdale is becoming a tech sales hub - The future of remote work and sales talent Whether you're just starting in tech sales or leading teams, this conversation delivers honest advice about avoiding common pitfalls and maximizing your potential in the industry. #techsales #saas #salescareer #techindustry #salesleadership #highticketsales #remotesales #remoteclosing #saassales CHAPTERS: 00:00 - Intro 01:00 - Javier's Introduction 03:20 - Will and Javier's Relationship 07:30 - WeWork and the Sales House Concept 12:45 - Vision Behind Glen Coco 17:21 - The Math and Strategy of Glen Coco 22:30 - Achievements of Will and Javier 24:35 - The Connection Between Sports and Sales 27:50 - Will's Journey to Glen Coco 30:30 - Personal Branding Tips and Advice 32:35 - Recognizing When to Move On 38:24 - Outro 39:17 - Finding Javier Online 39:50 - Outro Connect with Javier here, on LinkedIn.

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 essential tools, psychology, and tactics to crush your outreach game. Plus, get insider tips on crafting the perfect LinkedIn profile to boost your connection acceptance rate. Whether you're an SDR or AE looking to level up your prospecting skills, this episode is packed with actionable advice to help you close more deals. #techsales #videoprospecting #saas #sdr #ae Key topics: - The power of video in sales outreach - Essential tools for video prospecting (whiteboard, ring light, headset) - Optimizing your LinkedIn profile for higher acceptance rates - 3-step follow-up sequence for maximum impact - Time-blocking and batching video creation - Using video for introductions and proposals Don't miss out on this game-changing strategy that's helped me land meetings with top executives and close deals with big brands. Hit that like button, subscribe, and let me know what sales topics you want to hear next! #coldemail #leadgeneration #coldemailoutreach #videoprospecting #b2bleadgeneration CHAPTERS: 00:00 - Intro 00:27 - Why Video Prospecting 01:50 - Setup 06:52 - Psychology 07:57 - Video Prospecting on LinkedIn 12:35 - How to Create Effective Videos 17:09 - Video Prospecting Follow-Up Sequence 19:58 - Weekly Video Sending Strategy 20:32 - Time Management for Video Prospecting 22:43 - Optimizing LinkedIn Profile for Video Outreach 28:04 - Alternative Uses of Video 32:37 - Next Episode Shop all of the products I mentioned in this episode here, at my Amazon storefront. Download Loom for free, here.

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 position yourself for quick advancement. I share personal stories, practical tips, and insider advice that you won't find in paid courses. Whether you're breaking into tech sales or looking to level up, this episode is packed with actionable insights to supercharge your career. Ready to accelerate your path to AE? Hit play and let's dive in! #TechSales #SaaS #SDRtoAE #SalesCareer #StartupLife #techsales #saas #sdr #saassales #salesdevelopmentrepresentative CHAPTERS: 00:00 - Intro 02:12 - Join a Startup, Internal Networking 10:28 - Prospecting Strategies for Quota Success 12:21 - Triple Threat Tactic Explained 20:10 - Always Be Prospecting for Leads 21:56 - Triple Threat Prospecting Techniques 22:24 - Base Salary Mindset 23:19 - Final Thoughts and Takeaways Connect with me on LinkedIn here. Follow me on TikTok here. Subscribe to my YouTube here.

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 sales landscape. Learn how Logan transitioned from door-to-door sales to becoming a successful tech sales professional, and why he believes traditional sales experience is crucial for aspiring tech salespeople. We break down his proven networking strategies, including how he manages 7-8 events per month to build genuine relationships that convert to sales. Key topics we discuss: • Why door-to-door sales experience can accelerate your tech sales career • The truth about quota pressure and how to manage it • Building authentic relationships at networking events • The power of follow-up and why "fortune is in the follow-up" • Balancing work-life integration as a sales professional Whether you're looking to break into tech sales or level up your current sales career, this episode delivers actionable insights from someone who's walked the path and achieved real success. #techsales #saas #sales #networking #b2bsales #salesdevelopment #salescareer #b2bleadgeneration #objectionhandling #tipstoclosethesale #salestraining #businessdevelopment CHAPTERS: 00:00 - Intro 01:16 - Logan's Early Sales Experience 03:29 - Who is Logan Little 09:18 - Day-to-Day in Software Sales 11:28 - Logan's Role at His Company 13:07 - Logan's Travel Frequency 15:12 - Success at Networking Events 17:40 - Importance of Follow-Ups 21:00 - Adding Value in Follow-Ups 24:46 - Getting Client Referrals 28:14 - Making Buyers Say Yes 30:25 - Current vs Future State in Sales 35:00 - Misconceptions About Being an AE 39:57 - Lifelong Career in Sales 41:58 - Separating Work and Home Life 47:48 - Influential Figures in Logan's Life 51:00 - Common Seller Mistakes 54:28 - Connecting with Logan 55:39 - Outro You can connect with Logan on LinkedIn.

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 boost your connect rates • Using video to close more deals • Trends in cold calling for 2024 Plus, get Morgan's take on common mistakes reps make and who he looks up to in the industry. Whether you're new to tech sales or a seasoned AE, this episode is packed with actionable tips to level up your outreach game. #techsales #coldcalling #sdr #salessuccess Want more sales content? Follow Morgan @MorganJIngram on socials and check out his company amp for next-level content creation. #techsales #saassales #b2bsales #objectionhandling #permissionbasedopener#techsales #callopeningskills #liveprospectingcall #saassales #b2bsales CHAPTERS: 00:00 - Intro 02:13 - What Makes a Great SDR: Skills, Qualities, Success 05:20 - Morgan’s Foolproof Cold Call Opener: Techniques, Tips, Strategies 10:03 - What If They Say No: Handling Rejection, Objections, Responses 12:05 - Will’s Cold Call Opener: Effective Scripts, Engagement, Sales 15:20 - How Many Calls to Test: Metrics, Analysis, Optimization 16:45 - How Google News Will Affect Cold Calling: Trends, Impact, Adaptation 20:24 - How Morgan Uses Video in His Sales Process: Video Strategies, Engagement 21:00 - Why You Should Use Video in Your Sales Process: Benefits, Effectiveness 29:57 - Who Do You Look Up To: Inspiration, Mentorship, Role Models 32:06 - Number One Mistake Sales Reps Make: Common Pitfalls, Errors, Lessons 33:24 - The Best Advice Morgan Has Ever Given: Insights, Wisdom, Success Tips You can follow Morgan on LinkedIn here. You're going to love this episode!

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 vs. hybrid work models • Strategies for excelling in your tech sales role • Balancing content creation with a full-time sales career Learn how to crush your interviews, set more demos, and climb the tech sales ladder. Whether you're a recent grad or career-switcher, this episode is packed with actionable advice to help you break into and thrive in tech sales. #techsales #sdr #saas #salescareer #tiktok Want more tech sales content? Hit subscribe and let me know what topics you want covered next! #techsales #b2bsales #sdr #saassales #salesdevelopmentrepresentative #techsales #accountmanager #b2bsaas #transitioningtotechsales #saassales CHAPTERS: 00:00 - Intro 01:25 - Why Tech Sales: Benefits and Opportunities 06:14 - Previous Experience Before Tech Sales 12:26 - Staying Focused in Your Tech Sales Role 14:46 - Breaking Into Tech Sales in 2020: Tips and Strategies 19:27 - Job Applications: How Many Should You Submit Weekly? 21:55 - Weekly Messaging: How Many Messages to Send? 27:50 - Wealth University: Overview and Insights 31:50 - How to Enter Wealth University 32:30 - Challenges of Getting In: Overcoming Obstacles 33:20 - Closing the Interview: Tips for Success 35:00 - What to Do When Recruiters Say "We'll Get Back to You" 38:08 - Hybrid vs. Remote Work: Which is Better? 42:24 - Final Thoughts and Key Takeaways 49:56 - Employer Comments on Your Content: Navigating Feedback 54:37 - Brand Deals: Understanding Opportunities 56:57 - Role Models: Who Inspires You? 1:01:36 - Where to Find Sharif: Social Media and Contact Info Sharriff has over 84K followers on TikTok. You can follow him here.

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 success in today's market. Key topics we chop it up about: • Remote vs in-office work environments • Effective cold calling techniques • The evolution of buyer-seller dynamics • How to stand out in a crowded market Tom drops knowledge on building confidence, crafting compelling pitches, and making genuine connections with prospects. Whether you're new to sales or looking to level up your game, this episode is packed with actionable insights to help you excel in your tech sales career. #techsales #sdr #saas #coldcalling #salesstrategy #leadgeneration #saas #techsales #sdr #salesdevelopmentrepresentative CHAPTERS: 00:00 - Intro 02:45 - AE/BDR Relationship Insights 03:18 - Tom’s Experience & SD Lab Overview 08:11 - Remote vs In-Office Teams Discussion 13:44 - Introduction to RevGenius 19:10 - Value of In-Person Experiences 23:48 - Importance of Phone Communication Today 27:14 - Evolution of Buyers and Sellers 29:46 - Strategies for Cold Texting 33:20 - Effective Cold FaceTiming Techniques 37:08 - Avoiding Permission-Based Openers 39:49 - Will’s Cold Call Opener Strategy 42:50 - Tom’s Cold Call Opener Insights 46:05 - Booking Meetings Successfully 48:45 - Final Thoughts and Takeaways 52:30 - Personal Influences: Who Inspires You? 54:56 - Common Mistakes SDRs Make Today 57:30 - Connecting with Will and Tom Tom is the founder of the SD lab, you can find him at thesdlab.com You can also connect with him on LinkedIn!