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SellMeThisPen podcast
By SellMeThisPenEducation
SellMeThisPen podcast episodes
- #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/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/michaelocean/
Try 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.
1 hr 18 min - #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/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/michaelocean/
Try 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.
41 min - #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/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/michaelocean/
Try 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.
42 min - #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/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/michaelocean/
Try 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.
44 min - #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/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
48 min - #95 The 7-Step Playbook to Build Winning Sales Teams | Thomas Waites on SMTP Pod
About the episode:
In this episode, Michael and Thomas dive into what it really takes to build a winning sales culture from the ground up. They explore why sales success is less about natural talent and more about mindset, behavior, and creating systems that help any rep thrive—plus why being a good teammate matters just as much as closing deals.
About the guest:
Thomas Waites has spent his career building and scaling sales teams at startups, starting as the first employee after grad school and quickly moving into sales leadership within six months. He's led multiple successful acquisitions, most recently serving as CRO at Median before launching TW Sales, where he now works as a fractional CRO and advisor helping early-stage founders and sales leaders build winning cultures that drive explosive growth.
Where to find Thomas Waites:
https://www.linkedin.com/in/thomaswaites/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
49 min - #94 How AI is Transforming L&D: Compliance to Personalized Learning | Jen Rutsky on SMTP Pod
About the episode:
In this episode, Michael and Jen dive into how AI is transforming L&D and why embracing it is a game-changer for training teams. They explore practical ways to leverage AI for content creation, personalized learning, and why building an AI champion program helps drive real adoption across your organization.
About the guest:
Jen Rutsky is an L&D professional with over 15 years of experience across investment banking, law firms, and tech companies, and is currently leading learning and development at a FinTech company. She's a pioneer in AI-driven training, building AI champion programs and leveraging AI tools to create personalized learning experiences that scale across entire organizations.
Where to find Jen Rutsky:
LinkedInhttps://www.linkedin.com/in/jenniferrutsky/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
48 min - #93 How To Build a Culture-Driven Sales Team That Actually Wins | Kelly Breslin Wright on SellMeThisPen Pod
About the episode:
In this episode, Michael and Kelly dive into why culture-driven sales matters more than ever in the AI era and how authentic human connections trump vendor-first tactics. They explore why storytelling beats traditional sales methodologies, how AI will actually level the playing field and make your people your real differentiator, and why focusing on speed and efficiency alone could damage what makes your company special.
About the guest:
Kelly Breslin Wright is CEO & Founder at Culture Driven Sales. Prior she spent 12 years scaling Tableau Software from zero to $850 million in revenue as their first salesperson and eventual EVP of Sales, and later served as President and COO at Gong. Now she's teaching at business school, sitting on boards, and running Culture Driven Sales, where she helps companies put people and authentic connections at the heart of their go-to-market strategy instead of chasing speed at all costs.
Where to find Kelly Breslin Wright:
LinkedIn https://www.linkedin.com/in/kellybreslinwright/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
50 min - #92 How to Use AI to Maximize ROI in Insurance Sales | Martin Amador on SMTP Pod
About the episode:
Join Michael and Martin in this insightful podcast episode as they explore the future of insurance agencies in 2025. Discover how AI is revolutionizing the industry, the critical role of understanding your ROI, and how AI coaching tools can rapidly identify team challenges. Learn why prioritizing real client interactions over role-playing is essential for success in this dynamic field.
About the guest:
Martin Amador has been running his own insurance agency for eight years after making the leap from corporate retail and call center management, building processes and automation that let him focus on coaching and developing his team. He's passionate about using AI and data-driven tools to maximize ROI, speed up coaching, and help his agents develop the relationship skills that keep the insurance industry thriving.
Where to find Martin Amador:
LinkedIn: https://www.linkedin.com/in/denverinsurancepros/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
36 min - #91 Do This to Empower Your Sales Team in the Age of AI | Gail Behun on SMTP Pod
About the episode:
In this episode, Michael and Gail dive into why enablement is more critical than ever despite AI hype and recent industry upheaval. They talk about how enablement teams can prove their value, why building confidence and removing obstacles is at the core of the role, and how AI can actually empower enablement professionals to be more strategic instead of replacing them.
About the guest:
Gail Behun is a passionate enablement leader who transitioned from being a sales leader for nine years to founding her own practice, driven by her belief that enablement is a force multiplier when done right. She served as president of the Revenue Enablement Society until last year, where she connected with enablement professionals across the country and now advocates for the community through coaching, LinkedIn engagement, and helping both enablers and CROs maximize their impact together.
Where to find Gail Behun:
LinkedIn: https://www.linkedin.com/in/gailbehun/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: [email protected]
LinkedIn https://www.linkedin.com/in/michaelocean/
Try 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.
48 min
About SellMeThisPen podcast
From the publisher's feed
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.
In this podcast, SMTP's CEO and founder Michael Ocean is having conversations with top sales leaders and enablement experts to explore what it really takes to drive performance across go-to-market teams.