SellMeThisPen podcast

About the episode:

In this episode, Michael and Nate dive into the reality of change management in organizations. They discuss why successful implementation of change requires understanding both executive and employee perspectives, how leaders must clearly communicate the "why" behind change initiatives, and what happens when the pain of staying the same isn't enough to motivate meaningful transformation.

About the guest:

Nate Joseph is a seasoned sales leader with a journey that spans from hand-to-hand combat cold calling at Yelp to enterprise software at SAP, and now heads sales and partnerships at Twenty 5 in the SAP ecosystem. With extensive global experience in the SAP world and a background leading industry cloud strategy, Nate brings practical insights on implementing change management across organizations, particularly in technology adoption and digital transformation.

Where to find Nate Joseph:

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

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 Gal dive into the realities of buyer enablement in modern sales. They discuss why sales processes should focus on the buyer's journey rather than seller-centric stages, and how reps can become more valuable by helping customers navigate their complex internal buying process instead of just pushing products.

About the guest:

Gal Aga is a veteran B2B SaaS sales leader with 17 years in the trenches who scaled companies from $1 million to $100 million in ARR across roles as sales director, VP of sales, and CRO. He's now the CEO and co-founder of Aligned, where he's revolutionizing customer-facing collaboration through digital sales rooms designed to make buying easier and solve the complexity of modern sales processes.

Where to find Gal Aga:

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

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 Chris dive into the realities of individual coaching in sales. They discuss why effective coaching must focus on understanding customer problems rather than just product knowledge, how to build a coaching culture that avoids toxic group role-plays, and why waiting until reps fail before coaching them is a recipe for disaster.

About the guest:

Chris Nashed is a seasoned sales leader with over a decade of experience, specializing in taking early-stage startups beyond product-market fit. He's currently VP of Revenue at Goal, focusing on performance marketing for insurance agents, and previously spent six years at EverQuote where he helped scale their inside sales team through an IPO. Chris brings a coaching-focused leadership philosophy that emphasizes understanding customer problems first, building foundations for sales teams, and creating effective individual development paths rather than relying on outdated group role plays.

Where to find Chris Nashed:

LinkedIn: 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/⁠⁠

🌟 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 Pablo dive into the real impact of AI on sales teams. They discuss how implementing SellMeThisPen AI helped Ergeon increase bootcamp graduation rates from 60% to 90%, train 5x more reps simultaneously, and get new hires closing deals faster while allowing human coaches to focus on higher-value support.

About the guest:

Pablo Jaramillo is a performance coach at Ergeon. With a diverse background in soft skills training and team building he has helped grow their sales team 5X using AI-powered coaching tools. With previous experience running his own company and a unique blend of classical music training, Pablo now focuses on developing sales professionals through a holistic approach that combines mental health support, tactical skills improvement, and leveraging technology to enhance human performance.

Where to find Pablo Jaramillo:

LinkedIn: https://www.linkedin.com/in/pablo-jaramillo-7017819/ 

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 Yusuf dive into the power of one-on-one coaching in sales leadership. They explore why building personal relationships with team members creates trust that drives performance, how understanding reps' career aspirations is crucial for retention, and why effective leaders should prioritize these individual connections over group coaching sessions.

About the guest:

Yusuf Ongel has been in sales for over a decade, primarily focused on outbound lead generation, and has founded three businesses with one successful exit. He now leads XDR Hub, an outbound SDR services business that has grown 700-800% in just 15 months, and is passionate about one-on-one coaching as a fundamental leadership tool to build trust and develop his team.

Where to find Yusuf Ongel:

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

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 Ashton dive into the realities of running effective sales kickoffs and continuous enablement at scale. They discuss how Slack's successful SKO was built on in-person connections, cross-functional collaboration, and long-term reinforcement strategies, plus why focusing on seller confidence matters more than content.

About the guest:

Ashton Williams is a seasoned enablement leader with experience across education, training, and tech companies, currently serving as the Director of Slack Enablement at Salesforce and co-chair of Leadership Lounge at Sales Enablement Squad. After starting in customer success and leading partnerships at a sales association, she made her way into tech enablement in 2019 where she's been driving impactful initiatives and transforming how teams learn and operate at scale.

Where to find Ashton Williams:

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

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 Jocelle dive into the realities of sales onboarding and why a one-size-fits-all approach often fails. They explore how enablement's early involvement in hiring, continuous partnership with sales managers, and focus on individualized learning can transform the onboarding experience from a checkbox exercise into a foundation for long-term success.

About the guest:

Jocelle Sarenpa has been a sales professional since the age of 17, starting in retail jewelry sales before transitioning to tech, where she's become a prominent enablement leader and community builder. She currently serves as the co-director of RES Twin Cities, a founding ambassador, speaker, contributor, chapter lead for SEC, and a career coach and mentor, while being recognized as one of the enablement leaders to watch in 2023 and 2024.

Where to find Jocelle Sarenpa:

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

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 Jay dive into the realities of sales reinforcement and making training stick. They explore why microlearning and executive buy-in are crucial for success, how to leverage top performers as co-teachers, and why certification needs to go beyond just checking boxes.

About the guest:

Jay Shephard is a seasoned sales leader and value advisory expert with over two decades of experience in enterprise software and SaaS, specializing in transforming sales organizations through effective enablement strategies. He currently runs a sales value advisory consulting practice helping companies differentiate through value-driven solutions, after holding several enablement leadership roles where he developed innovative approaches to sales training and coaching.

Where to find Jay Shephard:

LinkedIn: https://www.linkedin.com/in/jay-shephard/ 

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 Eric dive into the realities of internal promotions and leadership development in sales. They explore why high performance alone isn't enough for promotion, how to identify true leadership potential beyond numbers, and why developing people daily beats one-off training events for building successful sales teams.

About the guest:

Eric Stavola is a seasoned leader with over 20 years of experience across digital transformation and business storytelling, who started in sales and evolved into executive roles including CEO and CIO positions. He's currently the VP of Managed Service Sales and Programs at Visual Edge, where he focuses on developing people through continuous coaching and education rather than traditional training, drawing from his experience as a football coach to help teams achieve better results.

Where to find Eric Stavola:

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

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 Hamish dive into the art of role-playing in sales. They discuss why practicing before real buyer interactions is crucial, how AI tools are changing the training game, and why group role-plays often do more harm than good. Hamish shares his proven framework for making one-on-one role-plays more effective and explains why coaching isn't a one-time event but an ongoing journey.

About the guest:

Hamish Knox started his career as a journalist at 16 before transitioning through marketing, PR, and sales, and has been a Sandler trainer since 2011 where he helps organizations achieve their revenue growth goals through coaching and training. He currently works with 7-figure companies looking to scale, guiding them through multi-year transformations while running Sandler Calgary and partnering with STS Capital to create successful exits.

Where to find Hamish Knox:

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

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.