SellMeThisPen podcast

About the episode:

In this episode, Michael and Vanessa dive into the real challenges of driving revenue impact through enablement and why data maturity is crucial for success. They explore how to build executive alignment, get frontline manager buy-in, and move beyond just training to create sustainable behavior change that actually sticks.

About the guest:

Vanessa Metcalf is the VP of Revenue Enablement at Showpad who started her career carrying a bag in sales before discovering enablement over a decade ago when it wasn't even a well-established field. She's since zigzagged through sales leadership, rev ops, and enablement roles at companies like Top Hat and Docebo, building her expertise in the trenches and becoming a passionate advocate for proving enablement's measurable impact on revenue.

Where to find Vanessa Metcalf: 

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

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 Michael Tristan explore how to scale enablement teams effectively while integrating AI and maintaining quality through rapid organizational changes. They dive into building global enablement operations, the art of upskilling your own team before serving others, and why a patient approach to AI adoption beats rushing into flashy tools.

About the guest:

Michael Tristan is the VP of Sales Enablement at Motive, where he leads a global team of nearly 40 people across the US and Pakistan, scaling enablement for a company approaching 450 million ARR and preparing for IPO. With a non-traditional background that includes training roles at Nordstrom and compliance work at Lyft, Michael has built his expertise around instructional design, leadership development, and AI-first enablement strategies that drive measurable results across enterprise sales organizations.

Where to find Michael Tristan: 

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

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 Marcus dive into the reality of AI adoption in sales organizations and why most teams aren't using it effectively despite knowing it's here to stay. They explore practical ways to lead AI implementation from the front, share specific prompts and frameworks for better deal management, and discuss how to cut through the noise in prospecting by focusing on relevancy over fancy personalization tricks.

About the guest:

Marcus Chan is a sales consultant and CEO of Venli Consulting who spent over 14 years in corporate America, getting promoted 12 times and hitting number one in every role before building a consultancy that helps organizations with 25+ AEs uncover millions in hidden revenue. With experience working with clients from startups to major companies like Salesforce, Google, and Microsoft, Marcus specializes in helping sales teams leverage AI and performance systems to drive results faster.

Where to find Marcus Chan: 

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

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 Matthew dive into the realities of going through layoffs and how it shapes your leadership style. They explore why reflecting on tough moments like RIFs can make you a better leader, the importance of playing offense instead of just fixing today's problems, and how experiencing a layoff firsthand teaches you to lead with more humanity and emotional intelligence.

About the guest:

Matthew Loria is a seasoned sales leader with over 15 years of experience across high-growth companies like Groupon, Salesforce, and now Sprout Social as VP of Sales, where he's been for nearly five years. Having personally navigated through layoffs and challenging market shifts, Matthew brings a uniquely human-centered approach to sales leadership, focusing on building resilient teams and creating environments where people genuinely want to fight to be there.

Where to find Matthew Loria:

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

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 Jose dive into the realities of implementing AI transformation at scale for enterprise sales teams. They discuss Jose's journey from evaluating six different AI vendors to successfully rolling out AI tools across a 100+ person sales team, including the challenges of getting buy-in from leadership and frontline managers, and why choosing the right implementation partner matters more than just the technology.

About the guest:

Jose Carranza is the Head of Sales at Ergeon, leading a team of 100+ sellers and driving AI transformation across the organization for over two years. Starting as an industrial engineer and working his way through various roles from manufacturing to analytics, Jose has become a pioneer in implementing AI-driven sales strategies, achieving remarkable results like reducing training time by 66% and reaching 70% AI-generated code at his company.

Where to find Jose Carranza:

LinkedIn: https://www.linkedin.com/in/jose-a-carranza-h/ 

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 Chloe dive into the real talk about customer success and why partnering with sales beats the traditional handoff approach. They explore what makes a great customer handoff, how to define success without overcomplicating it, and why everyone in the organization should own churn - not just CS teams.

About the guest:

Chloe Siegmann is a seasoned customer success leader with nearly 11 years at Houzz, where she currently serves as Head of Customer Success overseeing teams across the globe from onboarding to technical support. What makes her unique is her deep personal connection to Houzz's mission - her father was a residential architect, giving her firsthand insight into the struggles of home remodeling professionals that Houzz's platform aims to solve.

Where to find Chloe Siegmann:

LinkedIn: https://www.linkedin.com/in/chloe-siegmann/ 

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 Jordan dive into the practical side of sales enablement and how to actually tie it to revenue impact. They discuss why enablement teams should own specific numbers like ramp metrics and pipeline generation, how to create real-world certifications that reps can immediately apply, and why adapting to modern buying behaviors is more crucial than ever in today's AI-driven sales environment.

About the guest:

Jordan Timothy is a seasoned sales professional turned enablement leader with experience across companies like InsideSales, Pluralsight, Chargebee, and now Semrush as their enablement expert. With deep roots in sales and a passion for leveraging AI and data science to drive results, Jordan focuses on tying enablement directly to revenue impact through metrics like ramp time, pipeline generation, and deal velocity

Where to find Jordan Timothy:

LinkedIn: https://www.linkedin.com/in/jordan-timothy-35814770/ 

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 Haley dive into the realities of selling in service-based industries, exploring why buyers often mislead sellers and how having a solid process puts you on equal footing with prospects. They discuss the importance of being gutsy enough to run your own sales process, why sales managers need to get out of the field to make real observations, and how being wildly curious beats trying to convince people to buy.

About the guest:

Haley Haggerty is the president of Next Level Inc, a top 10 Sandler training franchise that's been around for 30 years, specializing in helping professional service organizations like consulting firms, engineering companies, and banks develop their sales capabilities. With two decades of experience training hundreds of professionals across 85+ industries, Haley focuses on empowering teams who "didn't go to school to be in sales" to build effective processes and overcome the mindset challenges that keep them from generating consistent business.

Where to find Haley Haggerty:

LinkedIn: https://www.linkedin.com/in/haley-haggerty-a403667/ 

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 Lawrence dive into why traditional sales enablement often fails and how shifting to buyer enablement can actually drive revenue. They discuss the importance of developing writing skills for modern sellers, creating scalable buyer persona frameworks, and why most of the deal happens outside of sales calls - plus Lawrence shares some hard-won lessons from building enablement programs from scratch.

About the guest:

Lawrence Wayne O’Connor is a seasoned sales enablement expert with over a decade of experience who has built three different enablement programs from the ground up, supporting over 80 sellers globally across companies ranging from Apple to startups. Based in North London as an expat from Chicago, Lawrence now runs an independent consultancy focused on shifting from traditional seller training to buyer enablement, helping organizations create systems that influence buyer decisions rather than just coaching call behavior.

Where to find Lawrence Wayne O’Connor:

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

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 Venkat dive into how AI can actually help build a coaching culture that lifts your entire sales team, not just the top performers. They explore why trust between sales leaders and reps is crucial, how to create psychological safety for trying new approaches, and why the shift from evaluation to enablement makes all the difference in getting real adoption.

About the guest:

Venkat Nagaswamy is a seasoned CRO at Splashtop with a fascinating journey from rocket scientist to sales leader, having founded multiple companies including an AI marketing startup that was acquired by 8x8. With over 15 years in sales leadership across tech companies like Mitel and 8x8, plus consulting experience at McKinsey, Venkat is passionate about using AI and data-driven approaches to elevate sales team performance and has been experimenting with ChatGPT to build custom coaching tools for his teams.

Where to find Venkat Nagaswamy:

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

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.