SellMeThisPen podcast

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 custome...

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...

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 be...

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 f...

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 adop...

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 gues...

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 quarte...

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 al...

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...

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 d...

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...

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 cre...

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 l...

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...

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 reinforcemen...

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...

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...

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 recogn...

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: Rachae...

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...

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...

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 futu...

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 ju...

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 j...

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...