#100 Why Your Best Salespeople Break Your Playbook (And That's Good) | Chris Nashed on SMTP Pod

#100 Why Your Best Salespeople Break Your Playbook (And That's Good) | Chris Nashed on SMTP Pod

About the episode: In this episode, Michael and Chris dive into why traditional role-playing is awkward and ineffective, and how AI-powered practice tools are changing the game for sales training. They explore the importance of framework-based selling over rigid playbooks, why most companies fail at enablement, and how adaptable reps with solid fundamentals are the ones who truly succeed across different environments. About the guest: Chris Nashed is a sales leader and revenue strategist who's been in the trenches building and scaling teams, currently serving as VP of Revenue at Goal while also founding RevGap. With deep hands-on experience in selling, coaching, and leveraging data-driven strategies, Chris is passionate about helping sales professionals and leaders optimize their approach using technology and AI. Where to find Chris Nashed: https://www.linkedin.com/in/chrisnashed/ [https://www.linkedin.com/in/chrisnashed/]  Where to find Michael (Founder & CEO @ SellMeThisPen AI): Email: ⁠⁠⁠michael@sellmethispen.ai⁠⁠⁠ [michael@sellmethispen.ai] LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/michaelocean/⁠⁠⁠ [https://www.linkedin.com/in/michaelocean/] Try SellMeThisPen AI @ ⁠⁠⁠https://www.sellmethispen.ai/⁠⁠⁠ [https://www.sellmethispen.ai/] At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨ Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations. The result? 👉 Faster onboarding 👉 Consistent methodology adoption 👉 Continuous skill development that scales across your entire team. Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.

#99 Connection-Centered Selling: Win Deals Without the Checklist | Barry Sowerwine on SMTP Pod

About the episode: In this episode, Michael and Barry dive into why traditional sales is fundamentally broken and how the industry has massively over-indexed on process while completely ignoring the art of human connection. They explore why passion and authentic storytelling beat methodologies every time, and what it takes to build unshakable belief across your entire go-to-market team. About the guest: Barry Sowerwine is a sales veteran with 35 years in the industry who helped 4 companies go public, most recently Tableau Software where he helped grow revenue from $10 million to over $800 million in seven years. He recently launched UnlockTheThing, pioneering a new category called "connection-centered selling" that focuses on the human side of sales—authentic connections and communication—rather than just process and methodology. Where to find Barry Sowerwine: https://www.linkedin.com/in/barry-sowerwine-69247a/ [https://www.linkedin.com/in/barry-sowerwine-69247a/]  Where to find Michael (Founder & CEO @ SellMeThisPen AI): Email: ⁠⁠⁠michael@sellmethispen.ai⁠⁠⁠ [michael@sellmethispen.ai] LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/michaelocean/⁠⁠⁠ [https://www.linkedin.com/in/michaelocean/] Try SellMeThisPen AI @ ⁠⁠⁠https://www.sellmethispen.ai/⁠⁠⁠ [https://www.sellmethispen.ai/] At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨ Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations. The result? 👉 Faster onboarding 👉 Consistent methodology adoption 👉 Continuous skill development that scales across your entire team. Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.

#98 The Death of Linear Sales Playbooks and What Will Work in 2026 | Greg Steward on SMTP Pod

About the episode: In this episode, Michael and Greg dive into what makes a good (or bad) enablement buyer and why flexibility matters more than following rigid sales playbooks. They explore how enablement has evolved from tactical training to strategic revenue impact, and why the human element can't be replaced by AI. About the guest: Greg Steward is a former gymnastics coach turned sales professional who's been selling enablement solutions for over 10 years, primarily to mid-market and enterprise clients. His unique background in coaching athletes gave him an unfair advantage connecting with enablement buyers, understanding that success in both fields comes down to building incremental skills and helping people achieve amazing outcomes. Where to find Greg Steward: https://www.linkedin.com/in/stewardgreg/ [https://www.linkedin.com/in/stewardgreg/]  Where to find Michael (Founder & CEO @ SellMeThisPen AI): Email: ⁠⁠⁠michael@sellmethispen.ai⁠⁠⁠ [michael@sellmethispen.ai] LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/michaelocean/⁠⁠⁠ [https://www.linkedin.com/in/michaelocean/] Try SellMeThisPen AI @ ⁠⁠⁠https://www.sellmethispen.ai/⁠⁠⁠ [https://www.sellmethispen.ai/] At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨ Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations. The result? 👉 Faster onboarding 👉 Consistent methodology adoption 👉 Continuous skill development that scales across your entire team. Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.

#96 How Adult Learning Principles Transform Sales Enablement | Rosi Young on SMTP Pod

About the episode: In this episode, Michael and Rosi chat about applying adult learning principles to sales enablement and why treating reps like humans instead of robots makes training actually stick. They explore how to balance data-driven approaches with the messy reality of how adults learn, and why understanding your audience matters more than perfect processes. About the guest: Rosi Young is a former secondary school teacher who pivoted into sales and has been crushing it in enablement for six years, working at major brands like Highspot, Gartner, and now Miro as the EMEA Enablement Lead. She brings a unique perspective to revenue enablement by applying adult learning principles from her teaching background to help sales teams retain knowledge and drive better results. Where to find Rosi Young: https://www.linkedin.com/in/rosiyoung/ [https://www.linkedin.com/in/rosiyoung/]  Where to find Michael (Founder & CEO @ SellMeThisPen AI): Email: ⁠⁠⁠michael@sellmethispen.ai⁠⁠⁠ [michael@sellmethispen.ai] LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/michaelocean/⁠⁠⁠ [https://www.linkedin.com/in/michaelocean/] Try SellMeThisPen AI @ ⁠⁠⁠https://www.sellmethispen.ai/⁠⁠⁠ [https://www.sellmethispen.ai/] At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨ Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations. The result? 👉 Faster onboarding 👉 Consistent methodology adoption 👉 Continuous skill development that scales across your entire team. Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.

#97 How to Coach Every Insurance Agent Daily Without Burnout (Using AI) | Bill Doran on SMTP Pod

About the episode: In this episode, Michael and Bill dive into the real talk about coaching sales teams and why AI tools should support—not replace—human coaches. They discuss how Bill learned from his early coaching mistakes, why practice shouldn't be about keeping score, and how AI can give coaches their time back to focus on what actually matters: developing their people. About the guest: Bill Doran has been crushing it in insurance sales for over 25 years and co-owns Diamond Guard Insurance Agency with his wife, where they've tripled their team size in just four years. He's a former CPA turned sales leader who's passionate about coaching and building high-performing teams through mentorship, AI tools, and a growth mindset focused on getting 1% better every day. Where to find Bill Doran: https://www.linkedin.com/in/diamondguardallstateagent/ [https://www.linkedin.com/in/diamondguardallstateagent/]  Where to find Michael (Founder & CEO @ SellMeThisPen AI): Email: ⁠⁠⁠michael@sellmethispen.ai⁠⁠⁠ [michael@sellmethispen.ai] LinkedIn ⁠⁠⁠https://www.linkedin.com/in/michaelocean/⁠⁠⁠ [https://www.linkedin.com/in/michaelocean/] Try SellMeThisPen AI @ ⁠⁠⁠https://www.sellmethispen.ai/⁠⁠⁠ [https://www.sellmethispen.ai/] At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨ Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations. The result? 👉 Faster onboarding 👉 Consistent methodology adoption 👉 Continuous skill development that scales across your entire team. Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.