About the episode:

In this episode, Michael and Laura dive into the realities of finding and maintaining product market fit, especially as companies scale and markets evolve rapidly. They explore why saying no to the wrong customers is crucial in early stages, how to track the right metrics at daily, weekly, and monthly intervals, and when to choose between PLG and sales-led motions without losing focus.

About the guest:

Laura Wheeler is a seasoned revenue operations and enablement expert with over 15 years of experience, having scaled teams at companies like Tableau (which she helped grow from $5M to $250M in the federal sector) and various startups from Series A through acquisition. She now is COO & Co-founder at RVNU, where she helps early-stage founders and C-level executives solve go-to-market challenges and accelerate growth through strategic revenue operations frameworks and product-market fit optimization.

Where to find Laura Wheeler:

LinkedIn: https://www.linkedin.com/in/wheels-revops/ 

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 Matt dive into the realities of sales coaching and why most managers aren't equipped to develop their teams effectively. They explore how to build intentional coaching cultures, why high performers leave when they don't get developed, and share some cringe-worthy stories of coaching gone wrong along the way.

About the guest:

Matt Benelli is a seasoned sales executive with over 25 years of experience, including 15.5 years at Oracle where he led teams from 6 to 600 people, followed by a decade running a successful Sandler training consultancy serving enterprise tech companies. Now he's the co-founder of CoachEm, an AI-powered coaching execution platform that helps sales managers become better coaches by focusing on the often-overlooked frontline manager as the key to sales team development.

Where to find Matt Benelli:

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

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 Joey dive into what really motivates AEs beyond just commission and how to build winning sales cultures at scale. They explore why transparency and being "in the details" as a leader trumps ivory tower management, plus Joey shares tactical insights on promotions, comp plan simplicity, and why AEs will work harder for better leads and recognition than just money.

About the guest:

Joey Nalevka is a revenue leader with over 15 years of experience exclusively focused on SMB sales, having held executive sales and operations leadership roles at companies like Groupon, Houzz, and Square. Starting his career after doubling sales performance at a telecommunications call center, Joey has since become known for bringing structure, discipline, and analytics to sales operations while helping both customers and team members achieve winning outcomes.

Where to find Joey Nalevka:

LinkedIn: https://www.linkedin.com/in/joey-nalevka-7b813917/ 

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 Rachael dive into the realities of building moats beyond technology in competitive markets. They discuss why listening to customer needs is crucial for adapting sales playbooks, how being agile drives success even after achieving market leadership, and why focusing on customer value is the ultimate defence against competitors.

About the guest:

Rachael Rose is a four-time growth stage executive with over two decades of experience helping companies grow and scale without breaking what makes them great. From crisis PR to leading cross-functional teams of up to 4,000 people across multiple industries including Groupon, health tech, real estate, and most recently Techstars, Rachael has built high-performing teams while owning P&Ls ranging from $10 million to $160 million.

Where to find Rachael Rose:

LinkedIn: https://www.linkedin.com/in/rachael-rose-8911795/ 

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 Josh dive into the evolving world of Customer Success enablement. They discuss the unique challenges CSMs face compared to sales teams, why CSMs need deeper product knowledge despite not being sellers, and how discovery skills remain crucial for both roles to drive strategic customer conversations.

About the guest:

Josh Scott is a seasoned enablement expert who transitioned from teaching music for 10 years to customer support, sales roles, and eventually enablement where he specialized in CS enablement at companies like Seismic. With experience building sales bootcamp programs and focused on customer success enablement for several years, Josh brings a unique perspective on how to effectively support CSMs in achieving their strategic goals while driving customer value.

Where to find Josh Scott:

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

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 Brian dive into the realities of inheriting sales teams as a new leader. They discuss why getting to know your people should always come first, how to identify and handle detractors on your team, and why coaching systems are crucial for developing high-performing reps through vulnerability and authentic leadership.

About the guest:

Brian Liebel is a seasoned sales leader with 15 years of experience, starting in B2C retail before transitioning to tech where he's worked with massive brands and startups through an outsourced SDR agency, HR payroll software, and spent four years at a sales coaching software company. He's currently leading the U.S. sales development team at 8x8, where he focuses on understanding his people first, removing roadblocks, and building cross-functional relationships with mutual action plans rather than just having standing meetings.

Where to find Brian Liebel:

LinkedIn: https://www.linkedin.com/in/brian-liebel-b6a079b1/ 

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 Konnor dive into the realities of scaling sales leadership from startup to growth stage. They discuss why human-focused coaching across multiple leadership levels beats playbook-only approaches, how value messaging continuity throughout the customer journey impacts retention, and why curiosity about AI is now a non-negotiable trait when building future-ready sales teams.

About the guest:

Konnor Martin is a seasoned VP of Sales who started his career in telecom before transitioning to tech, eventually joining RFPIO (now Responsive) as their fifth employee in 2017 and growing into leadership. With experience scaling a sales organization to 80-90 people globally while navigating the challenges of different growth stages, Konnor focuses on people-first leadership, coaching systems, and building unified value messaging across teams to drive retention in the age of AI disruption.

Where to find Konnor Martin:

LinkedIn: https://www.linkedin.com/in/konnor-martin-46611814/ 

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 Mike dive into the evolution of marketing and sales roles, exploring how they've become increasingly interconnected in today's digital landscape. They discuss why one-to-one engagement has made marketing more like hand-to-hand combat, the psychology behind effective LinkedIn conversations, and how sellers can bring genuine value instead of just pitching their services.

About the guest:

Mike Montague is a sales veteran with over 30 years of experience, starting his first professional sales class at age 15 and later spending 25 years at Sandler Training where he rewrote their global sales program used by over 50,000 people annually. After serving as Head of Franchise Strategy at Sandler he started Avenue9, where he helps people navigate AI for marketing strategy and audience engagement, bringing his unique perspective on the blending boundaries between sales and marketing in today's digital landscape.

Where to find Mike Montague:

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

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 Dave explore the realities of sales enablement leadership roles. They discuss what makes an effective enablement leader, why pushing back on executive requests is crucial, and how hiring the right enablement leader is critical as they'll set the foundation for the entire team - focusing on core skills like curiosity and adaptability rather than just industry-specific experience.

About the guest:

Dave Lichtman is a veteran sales enablement leader with over a decade of experience who transitioned from sales training into sales leadership before founding EnableMatch six and a half years ago. As the founder of EnableMatch, Dave now helps companies find and match with the right enablement talent, bringing his unique perspective on what makes a successful enablement professional after seeing patterns of struggles companies faced when trying to find effective enablement leaders.

Where to find Dave Lichtman: 

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

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 Mike dive into why traditional sales approaches aren't working in today's market. They discuss how focusing on buyer emotions rather than rigid sales processes, starting with conversations instead of demos, and targeting the 96% of non-active buyers can dramatically improve results over activity-based metrics that lack real impact.

About the guest:

Mike Conti is a seasoned sales leader with over 30 years of experience across early-stage, pre-IPO SaaS and technology companies. He challenges conventional sales methodologies that focus too heavily on activity without impact. Holding the position of CEO at AcceleraRev, Mike provides training on buyer-focused sales frameworks that align with how customers actually make decisions, helping teams move beyond the "activity without impact" trap to generate meaningful pipeline and achieve better conversion rates.

Where to find Mike Conti: 

LinkedIn: https://www.linkedin.com/in/mikeconti182/ 

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.