SellMeThisPen podcast

About the episode:

In this episode, Michael and Peter dive into the real challenges AEs face from onboarding to leadership dynamics. They explore why most onboarding programs miss the mark, how to run meaningful one-on-ones that go beyond pipeline reviews, and why sellers often feel like they're fighting battles both externally with customers and internally with their own teams.

About the guest:

Peter Schmitz is a Senior Strategic Account Executive at PeopleReign, a 17-person AI-focused company. With over a decade of experience at major companies like Tableau, Highspot, and Krisp, he has climbed from an entry-level role to strategic sales across six years and multiple territories. Peter brings a unique perspective shaped by his early days working in his parents' plant business where he learned the fundamentals of relationship-building and customer success that still drive his approach to sales today.

Where to find Peter Schmitz:

LinkedIn: https://www.linkedin.com/in/peter-james-schmitz/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Meredith dive into the realities of leading sales teams through the crucial first 90 days and beyond. They explore why listening before making changes is essential, how to build culture-add hiring strategies instead of culture-fit, and why creating bulletproof onboarding systems can turn new reps into quota crushers who hit 150% in their first quarter.

About the guest:

Meredith Chandler is currently a Head of Sales at Aligned, where she's built a powerhouse team with new AEs hitting 150%+ of quota in their first quarter through her systematic onboarding approach. With over 10 years in tech sales and startups including CaptivateIQ and pclub, Meredith also does one-on-one coaching and consulting, sharing her hard-won insights on LinkedIn and podcasts to help others avoid the mistakes she had to learn the hard way.

Where to find Meredith Chandler:

LinkedIn: https://www.linkedin.com/in/meredithchandler/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Carlie dive into the power of personal transformation and how overcoming life's biggest challenges can shape your career path in enablement. They discuss why getting crystal clear on what you want is crucial for job searching, how to think outside the box when prospecting for your dream role, and why aligning with a company's mission makes all the difference in finding fulfilment at work.

About the guest:

Carlie Chiarenza is a seasoned sales enablement professional who transformed her life and career after losing 125 pounds, which led her to discover her passion for motivating and training others. Currently serving as a Luxe Enablement Manager at Airbnb, Carlie has navigated through multiple enablement roles across startups and established companies, always advocating for her sales teams and bringing a unique perspective on resilience and personal growth to her enablement work.

Where to find Carlie Chiarenza:

LinkedIn: https://www.linkedin.com/in/carlie-chiarenza/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Ian dive into the real parallels between rescuing dogs and coaching salespeople, exploring how environment, patience, and personal motivation drive behavior change. They discuss why recognition often matters more than money for top performers, how to uncover individual goals that actually motivate people, and why managing down (prioritizing your team over your boss) creates the trust needed for effective coaching.

About the guest:

Ian Spandow is a seasoned sales enablement leader with over 35 years of experience across major tech companies like Oracle, MongoDB, and Riverbed, who has personally onboarded over 5,000 revenue professionals throughout his career. Beyond his corporate success, Ian runs a nonprofit dog rescue with his wife where they've rehabilitated over 250 high-risk dogs, applying the same principles of patience, positive reinforcement, and individual attention that make him effective at coaching struggling sales reps back to peak performance.

Where to find Ian Spandow:

LinkedIn: https://www.linkedin.com/in/ianspandow/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Meganne dive into how enablement professionals can get closer to customers to drive better business outcomes. They explore why stepping out from behind the scenes is crucial for enablement success, how to build alignment across all stakeholders from executives to end users, and why creating safe spaces for reps to practice and improve makes all the difference in driving real behavior change.

About the guest:

Meganne Brezina is a seasoned enablement leader with over a decade of experience scaling go-to-market teams at companies like Salesforce (ExactTarget), SAP (Emarsys), and Seismic (Lessonly), currently serving as Head of Enablement at Zylo. She brings a unique perspective to enablement having started as a seller of John Deere tractors and later co-running a restaurant, which taught her the critical importance of getting close to customers and understanding their real experiences with your team's delivery.

Where to find Julie Holmes:

LinkedIn: https://www.linkedin.com/in/meganne-brezina/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Julie dive into the reality of AI adoption in sales and why most organizations are still struggling despite all the hype. They explore how sales teams can practically leverage AI to solve their biggest time-wasting problems, why proper training and guidance are crucial to avoid costly mistakes, and how the 20-60-20 framework can help salespeople use AI as a powerful partner rather than a replacement.

About the guest:

Julie Holmes is a dynamic entrepreneur and AI strategist who travels the world delivering keynotes on making AI accessible to businesses and sales teams. With over 25 years in enterprise technology at companies like Oracle, JD Edwards, and PeopleSoft, plus multiple successful product launches including the first Bluetooth microphone for mobile phones, Julie now helps organizations embrace AI through her speaking, coaching, and her latest SaaS platform Stage Hopper for professional speakers.

Where to find Julie Holmes:

LinkedIn: https://www.linkedin.com/in/thejulieholmes/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael Ocean and Ned Arick dive into the reality of scaling revenue operations and why data-driven leadership beats gut feelings every time. They explore how to have tough conversations with boards about realistic targets, why starting with front-line reps is crucial for successful change management, and how building accountability culture from the top down creates teams that actually hit their numbers.

About the guest:

Ned Arick is a proven CRO and sales leader who built his company Beam from zero to eight figures in 18 months before selling to private equity, and now leads revenue operations for a 250-person organization overseeing marketing, sales, and customer success teams of nearly 100 people. Starting from strength coaching aspirations to Silicon Valley startups, then consulting at ClozeLoop, Ned has become a data-driven revenue expert who focuses on systems, processes, and accountability rather than just adding headcount to hit numbers.

Where to find Ned Arick:

LinkedIn: https://www.linkedin.com/in/nedarick/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael Ocean and John Barrows dive into the harsh realities of today's sales org structure and why the traditional SDR model is fundamentally broken in 2025. They discuss the massive shift needed from predictable revenue tactics to AI-native approaches, why inbound SDRs should be eliminated entirely, and how to transform your team through collaborative AI labs that actually develop real sales skills instead of just activity metrics.

About the guest:

John Barrows is a veteran sales leader and consultant with over 25 years of experience who's been in the trenches at companies like DEWALT and Xerox, and now runs JB Sales where he helps organizations transform their go-to-market strategies in the AI era. Known for his no-nonsense approach, John challenges the traditional SDR model and advocates for fundamental changes to how we structure and develop sales teams in today's market.

Where to find John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Mo'men dive into the realities of coaching sales teams across different cultures and seller personas. They explore how to build trust with seasoned reps, why understanding your team's background matters more than jumping straight into coaching, and the smart approach of observing first before making changes to avoid costly mistakes.

About the guest:

Mo'men Amin is a seasoned sales professional with over 20 years of experience spanning from family business roots to corporate leadership roles across Canadian, American, and Egyptian markets, currently serving as Commercial Director for a US construction company while running a successful side hustle helping Egyptian startups build winning sales teams. Beyond his corporate achievements, Mo'men is also a sales author, vlogger, and coach who brings a unique cross-cultural perspective to sales leadership and team development.

Where to find Mo'men Amin:

LinkedIn: https://www.linkedin.com/in/mo-men-amin-a3b973b3/?originalSubdomain=eg 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.

About the episode:

In this episode, Michael and Phil dive into the realities of cross-functional alignment in sales organizations and why training managers instead of reps often delivers better results. They discuss practical strategies for building psychological safety through film reviews, the importance of understanding how product and marketing teams actually work, and why ongoing reinforcement beats one-time training every time.

About the guest:

Phil Rapisardo is a seasoned go-to-market leader with over 15 years of experience across multiple functions at companies like Groupon and Reputation, where he wore nearly every hat from sales engineer to enterprise sales leader, product marketing, and enablement. Currently between roles, Phil is passionate about building high-performing sales teams through innovative coaching methods like film reviews and cross-functional collaboration that drives real results.

Where to find Phil Rapisardo:

LinkedIn: https://www.linkedin.com/in/philrapisardo/ 

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/⁠⁠

🌟 SellMeThisPen AI is the only all-in-one AI sales coaching platform that helps sellers in every step of their journey.

Before client calls - Role-play realistic sales conversations with AI to perfect your pitch and practice objection handling, without burning precious leads.

During client calls - Receive real-time guidance to handle objections consistently and get reminded to ask the right questions so you can win deals faster.

After client calls - Get unbiased feedback so you can improve next time. And it doesn't stop there—SMTP takes care of your notes and CRM updates so you can focus on selling instead of admin work.