SellMeThisPen podcast

About the episode: In this episode, Michael and Chris dive into why traditional role-playing is awkward and ineffective, and how AI-powered practice tools are changing the game for sales training. They explore the importance of framework-based selling over rigid playbooks, why most companies fail at enablement, and how adaptable reps with solid fundamentals are the ones who truly succeed across di...

About the episode: In this episode, Michael and Barry dive into why traditional sales is fundamentally broken and how the industry has massively over-indexed on process while completely ignoring the art of human connection. They explore why passion and authentic storytelling beat methodologies every time, and what it takes to build unshakable belief across your entire go-to-market team. About the...

About the episode: In this episode, Michael and Greg dive into what makes a good (or bad) enablement buyer and why flexibility matters more than following rigid sales playbooks. They explore how enablement has evolved from tactical training to strategic revenue impact, and why the human element can't be replaced by AI. About the guest: Greg Steward is a former gymnastics coach turned sales pro...

About the episode: In this episode, Michael and Rosi chat about applying adult learning principles to sales enablement and why treating reps like humans instead of robots makes training actually stick. They explore how to balance data-driven approaches with the messy reality of how adults learn, and why understanding your audience matters more than perfect processes. About the guest: Rosi Young is...

About the episode: In this episode, Michael and Bill dive into the real talk about coaching sales teams and why AI tools should support—not replace—human coaches. They discuss how Bill learned from his early coaching mistakes, why practice shouldn't be about keeping score, and how AI can give coaches their time back to focus on what actually matters: developing their people. About the guest: B...

About the episode: In this episode, Michael and Thomas dive into what it really takes to build a winning sales culture from the ground up. They explore why sales success is less about natural talent and more about mindset, behavior, and creating systems that help any rep thrive—plus why being a good teammate matters just as much as closing deals. About the guest: Thomas Waites has spent his career...

About the episode: In this episode, Michael and Jen dive into how AI is transforming L&D and why embracing it is a game-changer for training teams. They explore practical ways to leverage AI for content creation, personalized learning, and why building an AI champion program helps drive real adoption across your organization. About the guest: Jen Rutsky is an L&D professional with over 15...

About the episode: In this episode, Michael and Kelly dive into why culture-driven sales matters more than ever in the AI era and how authentic human connections trump vendor-first tactics. They explore why storytelling beats traditional sales methodologies, how AI will actually level the playing field and make your people your real differentiator, and why focusing on speed and efficiency alone co...

About the episode: Join Michael and Martin in this insightful podcast episode as they explore the future of insurance agencies in 2025. Discover how AI is revolutionizing the industry, the critical role of understanding your ROI, and how AI coaching tools can rapidly identify team challenges. Learn why prioritizing real client interactions over role-playing is essential for success in this dynamic...

About the episode: In this episode, Michael and Gail dive into why enablement is more critical than ever despite AI hype and recent industry upheaval. They talk about how enablement teams can prove their value, why building confidence and removing obstacles is at the core of the role, and how AI can actually empower enablement professionals to be more strategic instead of replacing them. About the...

About the episode: In this episode, Michael and Dina break down the real stages of change management and why most transformation projects fail before they even start. They explore how to gain leadership buy-in beyond just "we need AI," why enablement needs to manage up with data instead of gut feelings, and how to create actual adoption instead of just rolling out more training that nobo...

About the episode: In this episode, Michael and Bryan dive into how insurance agencies can thrive in an increasingly regulated and competitive market by embracing AI and building a culture of continuous learning. They discuss why process beats price in today's landscape, how to get buy-in from skeptical high performers, and why AI tools should amplify leaders rather than replace them. About th...

About the episode: In this episode, Michael and Tim dive into why account management is the most underappreciated role in SaaS and how to fix it. They discuss why AMs need to be in the room from day one, how to turn around at-risk accounts, and why companies need to start investing in post-sales teams the same way they invest in new business acquisition. About the guest: Tim Work is a Senior Direc...

About the episode: In this episode, Michael and Iulia dive into the identity crisis of RevOps and why it's stuck between strategic planning and endless admin work. They explore how to roll out AI tools the right way, why adoption beats features every time, and how fractional RevOps is becoming the new normal for companies doing more with less. About the guest: Iulia Tesfai is a seasoned RevOps...

About the episode: In this episode, Michael and Lisa dive into selling through downturns and why investing in people beats playing not to lose. They explore how to authentically rebrand yourself on LinkedIn, the power of understanding your buyers deeper than the competition, and why account managers need to be strategic ninjas who know more about customers and competitors than anyone else. About t...

About the episode: In this episode, Michael and Kate dive into the realities of implementing AI in sales enablement, from building foundational knowledge before jumping into tools to managing the challenge of reps using their own AI solutions. They explore why starting with education beats rushing into adoption, how to measure real behavior change beyond just usage metrics, and why treating AI imp...

About the episode: In this episode, Michael and Shannon dive into the real talk about win-loss analysis and how to turn raw data into actionable insights that actually help sales teams close more deals. They explore why you need multiple data sources beyond CRM notes, how to build cross-functional alignment around customer feedback, and why giving sellers less content with more context beats drown...

About the episode: In this episode, Michael and Matt dive into navigating AI transformation as a sales leader and why authentic human connections still matter most. They discuss how to stay relevant in a rapidly changing landscape, the importance of face-to-face meetings over endless AI tools, and why being genuinely curious and real with customers beats any sales trick in the book. About the gues...

About the episode: In this episode, Michael and Rob dive into the evolving world of sales development and how AI is reshaping the game. They explore the balance between human connection and AI augmentation, why outbound is getting harder in today's noisy market, and how to build SDR teams that actually drive pipeline instead of just booking meetings. About the guest: Rob Lotzer is a seasoned s...

About the episode: In this episode, Michael and Nina dive into the realities of building enablement programs that actually drive behavior change and business impact. They explore why manager buy-in is crucial for sustainable success, how to design programs that stick beyond the initial rollout, and share a real case study of a career development program that achieved 70% promotion success through...

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 En...

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...

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...

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 emotion...

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...