Shows
SellMeThisPen podcast#100 Why Your Best Salespeople Break Your Playbook (And That's Good) | Chris Nashed on SMTP PodAbout 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 different environments.About the guest:Chris Nashed is a sales leader and revenue strategist who's been in the trenches building and scaling teams, currently serving as VP of Revenue at...
2025-12-301h 17SellMeThisPen podcast#99 Connection-Centered Selling: Win Deals Without the Checklist | Barry Sowerwine on SMTP PodAbout 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 guest:Barry Sowerwine is a sales veteran with 35 years in the industry who helped 4 companies go public, most recently Tableau Software where he helped grow revenue from $10 million to over $800...
2025-12-2240 minSellMeThisPen podcast#98 The Death of Linear Sales Playbooks and What Will Work in 2026 | Greg Steward on SMTP PodAbout 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 professional who's been selling enablement solutions for over 10 years, primarily to mid-market and enterprise clients. His unique background in coaching athletes gave him an unfair advantage...
2025-12-1141 minSellMeThisPen podcast#96 How Adult Learning Principles Transform Sales Enablement | Rosi Young on SMTP PodAbout 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 a former secondary school teacher who pivoted into sales and has been crushing it in enablement for six years, working at major brands like Highspot, Gartner, and now...
2025-12-0443 minSellMeThisPen podcast#97 How to Coach Every Insurance Agent Daily Without Burnout (Using AI) | Bill Doran on SMTP PodAbout 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:Bill Doran has been crushing it in insurance sales for over 25 years and co-owns Diamond Guard Insurance Agency with his wife, where they've tripled thei...
2025-12-0447 minSellMeThisPen podcast#95 The 7-Step Playbook to Build Winning Sales Teams | Thomas Waites on SMTP PodAbout 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 building and scaling sales teams at startups, starting as the first employee after grad school and quickly moving into sales le...
2025-11-2648 minSellMeThisPen podcast#94 How AI is Transforming L&D: Compliance to Personalized Learning | Jen Rutsky on SMTP PodAbout 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 years of experience across investment banking, law firms, and tech companies, and is currently leading learning and development at a FinTech company. She's a pioneer...
2025-11-1747 minSellMeThisPen podcast#93 How To Build a Culture-Driven Sales Team That Actually Wins | Kelly Breslin Wright on SellMeThisPen PodAbout 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 could damage what makes your company special.About the guest:Kelly Breslin Wright is CEO & Founder at Culture Driven Sales. Prior she spent 12 years scaling Tableau Software from zero...
2025-11-0649 minSellMeThisPen podcast#92 How to Use AI to Maximize ROI in Insurance Sales | Martin Amador on SMTP PodAbout 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 field.About the guest:Martin Amador has been running his own insurance agency for eight years after making the leap from corporate retail and call center management, building processes and...
2025-11-0335 minSellMeThisPen podcast#91 Do This to Empower Your Sales Team in the Age of AI | Gail Behun on SMTP PodAbout 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 guest:Gail Behun is a passionate enablement leader who transitioned from being a sales leader for nine years to founding her own practice, driven...
2025-10-2847 minSellMeThisPen podcast#90 Why 1/3 of Change Programs Fail (And How to Fix Yours) | Dina Berger on SMTP PodAbout 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 nobody uses.About the guest:Dina Berger is a sales enablement veteran with over 11 years of experience who made an unconventional career pivot from university...
2025-10-2840 minSellMeThisPen podcast#89 The Future of Insurance Sales: AI, Training & Leadership | Bryan Dinklenburg on SMTP PodAbout 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 the guest:Bryan Dinklenburg is the Director of Operations at L&T Agency Group Inc, where he's been since 2005, with a BA in organizational leadership from Arizona State...
2025-10-2133 minSellMeThisPen podcast#88 Account Management is the New Sell: Why You Must Invest Now | Tim Work on SMTP PodAbout 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 Director at Actabl with 20 years of experience in sales leadership, specializing in account management and customer success across...
2025-10-1539 minSellMeThisPen podcast#87 Why RevOps Have an Identity Crisis (And How to Fix It) | Iulia Tesfai on SMTP PodAbout 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 professional with over 15 years of experience across SaaS companies in SaaS and supply chain, and recently transitioned to full-time fractional Head of...
2025-10-0843 minSellMeThisPen podcast#86 Selling Through Downturns: Relationships Beat Cost Cutting | Lisa Honaker on SMTP PodAbout 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 the guest:Lisa Honaker is a seasoned revenue leader with over 30 years of experience across Fortune 100 companies like FedEx and SaaS organizations including Highspot and Actabl, where...
2025-09-3041 minSellMeThisPen podcast#85 Why Banning AI Tools Will Backfire: Building Safe AI Adoption | Kate Stringfield on SMTP PodAbout 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 implementation like any other sales methodology requires proper change management and integration across the entire organization.About the guest:Kate Stringfield is a reformed seller turned enablement expert...
2025-09-2438 minSellMeThisPen podcast#84 Stop Drowning Sellers in Content: Win-Loss Analysis Secret | Shannon Izquierdo on SMTP PodAbout 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 drowning them in materials they'll never use.About the guest:Shannon Izquierdo is founder of the Prompt Insight Group, a consulting company focused on enablement and branding...
2025-09-2248 min
SellMeThisPen podcast#83 The One Thing AI Will Never Replace in Enterprise Sales | Matt Marshall on SMTP PodAbout 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 guest:Matt Marshall is a startup sales veteran with over 20 years of experience scaling teams at companies like Embarcadero, Successfactors, Citrix, and Iterable, where he helped...
2025-09-2235 minSellMeThisPen podcast#82 AI Won't Replace SDRs But This Will Transform Sales Development | Rob Lotzer on SMTP PodAbout 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 sales development leader with extensive experience across major SaaS companies like Salesforce and various startups, currently leading North American SDR and BDR organizations at...
2025-09-2242 minSellMeThisPen podcast#81 How to Build Sales Enablement That Actually Drives Behavior Change | Nina LaRouche on SMTP PodAbout 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 strategic champion building and peer-to-peer learning.About the guest:Nina LaRouche is a seasoned enablement leader with over a decade of experience who has built programs from the ground...
2025-09-1343 min
SellMeThisPen podcast#80 Why Enablement Without Data is Just Expensive Training | Vanessa Metcalf on SellMeThisPen PodAbout 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...
2025-08-2548 minSellMeThisPen podcast#79 Building a Global Sales Team: Leveraging Teams and AI | Michael Tristan on SellMeThisPen PodAbout 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...
2025-08-1237 minSellMeThisPen podcast#78 The AI Discovery Framework That Wins Enterprise Deals | Marcus Chan on SellMeThisPen PodAbout 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...
2025-08-0746 minSellMeThisPen podcast#77 The Human Side of RIFs: What Most Sales Leaders Get Wrong | Matthew Loria on SellMeThisPen PodAbout 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...
2025-08-0739 minSellMeThisPen podcast#76 From 6 Weeks to 2 Weeks Training: AI Sales Training Success | Jose Carranza on SellMeThisPen PodAbout 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...
2025-07-3153 minSellMeThisPen podcast#75 Building Sales & CS Alignment That Reduces Churn | Chloe Siegmann on SellMeThisPen PodAbout 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...
2025-07-3141 minSellMeThisPen podcast#74 The Revenue Impact of Sales Enabler: Ramp, Pipeline & Velocity | Jordan Timothy on SellMeThisPen PodAbout 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...
2025-07-3146 minSellMeThisPen podcast#73 The #1 Sales Leadership Mistake: Feedback vs. Observation | Haley Haggerty on SellMeThisPen PodAbout 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...
2025-07-3148 minSellMeThisPen podcast#72 Buyers Spend 6% of Time With Your Sales Team: Don't Waste It | Lawrence Wayne on SellMeThisPen PodAbout 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 di...
2025-07-3144 minSellMeThisPen podcast#71 Stop Forcing Tools on Your Team - Do This Instead | Venkat Nagaswamy on SellMeThisPen PodAbout 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...
2025-07-3144 minSellMeThisPen podcast#70 The Sales Metrics Mistake That Ruins Your Team's Performance | Peter Schmitz on SellMeThisPen PodAbout 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 guest:Peter Schmitz is a Senior Strategic Account Executive at PeopleReign, a 17-person AI-focused company. With over a decade of experience at major companies like Tableau, Highspot, and Krisp...
2025-07-3151 minSellMeThisPen podcast#69 Culture Add vs Culture Fit: Building Winning Sales Teams | Meredith Chandler on SellMeThisPen PodAbout 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 quarter.About the guest:Meredith Chandler is currently a Head of Sales at Aligned, where she's built a powerhouse team with new AEs hitting 150%+ of quota in their first quarter...
2025-07-3143 minSellMeThisPen podcast#68 Job Search Strategy That Gets Interviews at Zoom & Airbnb | Carlie Chiarenza on SellMeThisPen PodAbout 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 all the difference in finding fulfilment at work.About the guest:Carlie Chiarenza is a seasoned sales enablement professional who transformed her life and career after...
2025-07-3132 minSellMeThisPen podcast#67 The Truth About What Really Motivates Top Salespeople | Ian Spandow on SellMeThisPen PodAbout 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 over your boss) creates the trust needed for effective coaching.About the guest:Ian Spandow is a seasoned sales enablement leader with over 35 years of experience across major tech companies like Oracle...
2025-07-3141 minSellMeThisPen podcast#66 Why Sales Enablement Must Get Customer-Facing | Meganne Brezina on SellMeThisPen PodAbout 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 difference in driving real behavior change.About the guest:Meganne Brezina is a seasoned enablement leader with over a decade of experience scaling go-to-market teams at...
2025-07-3143 minSellMeThisPen podcast#65 Stop Training AI Tools - Start Building AI Mindsets in Sales | Julie Holmes on SellMeThisPen PodAbout 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 AI as a powerful partner rather than a replacement.About the guest:Julie Holmes is a dynamic entrepreneur and AI strategist who travels the world...
2025-07-3134 minSellMeThisPen podcast#64 Stop Guessing Your Sales Team Needs: Let Data Drive Your Coaching | Ned Arick on SellMeThisPen PodAbout 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 creates teams that actually hit their numbers.About the guest:Ned Arick is a proven CRO and sales leader who built his company Beam from zero to eight figures in 18...
2025-07-3149 minSellMeThisPen podcast#63 The Death of Traditional SDR Roles: What's Next for Sales Teams | John Barrows on SellMeThisPen PodAbout 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 labs that actually develop real sales skills instead of just activity metrics.About the guest:John Barrows is a veteran sales leader and consultant with over 25 years of experience who's...
2025-07-3143 minSellMeThisPen podcast#62 Why Smart Sales Leaders Invest Time in Coaching | Mo'men Amin on SellMeThisPen PodAbout 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 guest:Mo'men Amin is a seasoned sales professional with over 20 years of experience spanning from family business roots to corporate leadership roles across Canadian, American, and Egyptian markets, currently serving...
2025-07-3134 minSellMeThisPen podcast#61 The Manager Layer: Secret to Perfect Team Alignment | Phil Rapisardo on SellMeThisPen PodAbout 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 reinforcement beats one-time training every time.About the guest:Phil Rapisardo is a seasoned go-to-market leader with over 15 years of experience across multiple functions at companies like Groupon and Reputation, where he wore nearly every...
2025-07-3138 minSellMeThisPen podcast#60 Why Product-Market Fit is a Process, Not a Moment | Laura Wheeler on SMTP PodAbout 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...
2025-07-3143 minSellMeThisPen podcast#59 Coaching Cultures Keep Top Talent Longer | Matt Benelli on SellMeThisPen PodAbout 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...
2025-07-3144 minSellMeThisPen podcast#58 What AEs Really Want More Than Money (Building Winning Culture) | Joey Nalevka on SellMeThisPen PodAbout 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...
2025-07-3136 minSellMeThisPen podcast#57 Building a Sales Moat in a Crowded Market | Rachael Rose on SellMeThisPen PodAbout 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...
2025-07-3132 minSellMeThisPen podcast#56 Bridging Sales & CS: The Future of Revenue Enablement | Josh Scott on SellMeThisPen PodAbout 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...
2025-07-3143 minSellMeThisPen podcast#55 Building Winning Sales Teams: People First, Always | Brian Liebel on SellMeThisPen PodAbout 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...
2025-07-3147 minSellMeThisPen podcast#54 Why People Leadership Beats Playbooks in Today's Sales World | Konnor Martin on SellMeThisPen PodAbout 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...
2025-07-3147 minSellMeThisPen podcast#53 Why Marketing and Sales Should Be in Alignment | Mike Montague on SellMeThisPen PodAbout 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...
2025-07-3144 minSellMeThisPen podcast#52 How to Identify and Hire Enablement Leaders That Drive Revenue | Dave Lichtman on SellMeThisPen PodAbout 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...
2025-07-3145 minSellMeThisPen podcast#51 The Demo-First Approach Is Your Best Pipeline Killer | Mike Conti on SellMeThisPen PodAbout 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...
2025-07-3152 minSellMeThisPen podcast#50 How to Coach Sellers Who Don't Want Help (Proven Tactics) | Edward Cannon on SellMeThisPen PodAbout the episode:In this episode, Michael and Ed dive into sales enablement and the power of tactical support. They discuss the importance of building individual relationships with sellers, understanding their unique motivations, and providing hands-on help rather than just theoretical training. Ed shares his journey from sales to enablement, emphasizing how empathy, timing, and being genuinely helpful are the keys to successful enablement.About the guest:Edward Cannon is a seasoned sales enablement professional with over 3 years of dedicated experience, who transitioned from enterprise sales at Verizon to sales...
2025-07-3140 minSellMeThisPen podcast#49 Data-Driven Sales Leadership: Turning B-Players into Top Performers | Guy Rubin on SellMeThisPen PodAbout the episode:In this episode, Michael and Guy dive into the latest Ebsta benchmark report on sales performance. They explore why just 14% of sellers are responsible for 80% of revenue, how top performers qualify deals earlier based on ICP, and why data-driven consistency across sales processes is the key to transforming B and C players into quota-crushers.About the guest:Guy Rubin is a passionate sales and data leader who founded Ebsta, a revenue intelligence platform with nearly 400 customers that's focused on solving data quality issues in Salesforce and providing...
2025-07-3145 minSellMeThisPen podcast#48 Leadership Development: From Tactical Manager to Leader | Jenny Floros on SellMeThisPen PodAbout the episode:In this episode, Michael and Jenny dive into the realities of leadership development for mid-level managers. They discuss why embracing both tactical management and true leadership is crucial for company growth, how good mentors can transform career trajectories, and why intentional time management is the secret weapon for today's overwhelmed managers.About the guest:Jenny Floros is a seasoned leadership development expert with over three decades of experience across live entertainment ticketing, tech startups, and an 11-year journey at Groupon where she discovered her passion for developing...
2025-07-3148 minSellMeThisPen podcast#47 AI Implementation That Actually Drives Sales Results | Steve Smith on SellMeThisPen PodAbout the episode:In this episode, Michael and Stephen dive into the realities of implementing AI in organizations. They discuss how to drive user adoption through leadership involvement, why starting with practical use cases beats broad implementation, and the importance of creating a culture where experimentation with AI tools is encouraged and celebrated.About the guest:Stephen Smith is a technology and strategy veteran with over 30 years of experience across tech companies, startups, and consulting firms, having served as CEO, CFO, and SVP of RevOps before transitioning to focus exclusively...
2025-07-3135 minSellMeThisPen podcast#46 Sales Coaching Mastery: The Art of Asking the Right Questions | Kieran Smith on SellMeThisPen PodAbout the episode:In this episode, Michael and Kieran dive into the realities of sales coaching and what it really takes to develop high-performing reps. They discuss why quality questions trump feedback dumps, how true coaching creates psychological safety through self-reflection, and why the fundamentals of curiosity and consistency matter more than chasing silver bullets in today's tough market.About the guest:Kieran Smith is a seasoned sales enablement expert with 17+ years in the sales world, starting as a frontline seller and spending over a decade in sales leadership before...
2025-07-3145 minSellMeThisPen podcast#45 Authentic Leadership: Building Lasting Impact | Teri Long on SellMeThisPen PodAbout the episode:In this episode, Michael and Teri dive into what makes authentic leaders successful in enablement. They discuss why getting your hands dirty with frontline teams is crucial, how leaders who don't have all the answers build stronger organizations, and why AI will enhance productivity but never replace the human connection at the heart of sales.About the guest:Teri Long is the VP of GTM Revenue & Customer Enablement at Mindtickle and an award-winning sales enablement leader, receiving the Selling Power Enablement Excellence Awards in 2023 and 2024. With over 25...
2025-07-3134 minSellMeThisPen podcast#44 Stop Limiting Enablement to Sales Teams Only | Matt Schalsey on SellMeThisPen PodAbout the episode:In this episode, Michael and Matt dive into the parallels between recruitment and sales processes. They discuss why recruiters are essentially sales professionals selling company vision, how bad hiring directly impacts enablement efforts, and why improving recruitment processes with better questions and AI assistance can help teams hire for roles instead of just filling seats.About the guest:Matt Schalsey is an award-winning Go-To-Market advisor and the CEO & Founder of Perfect Hire, where he's developing an AI-infused Applicant Relationship Manager that combines ATS and CRM functionalities to...
2025-07-3142 minSellMeThisPen podcast#43 Why Change Management Is A Critical Skill in Sales Enablement | Crystal Nikosey on SellMeThisPen PodAbout the episode:In this episode, Michael and Crystal dive into the realities of change management in sales enablement. They discuss why understanding company culture is critical before implementing new frameworks, how to get leadership buy-in across all levels, and why competency-led frameworks are essential for measuring behavior change and creating effective coaching cultures.About the guest:Crystal Nikosey is a dedicated enablement professional with over eight years of experience who transitioned from carrying a bag as a seller to becoming @Your_Favorite_Enabler across various social platforms. With a...
2025-07-3141 minSellMeThisPen podcast#42 70% of Buyers Avoid Salespeople - How To Be In The 30% | Steve Reid on SellMeThisPen PodAbout the episode:In this episode, Michael and Steve dive into the real world of sales transformation and leadership. They discuss why modern buyers have fundamentally changed their expectations, how traditional product-focused selling is failing, and why the most successful salespeople approach selling as problem-solving rather than feature-dumping to create authentic value for customers.About the guest:Steve Reid is a seasoned sales leader with over 30 years of experience who transitioned from marketing to sales leadership, eventually scaling a company to $50 million before a successful exit. Currently, as the founder...
2025-07-3146 minSellMeThisPen podcast#41 Better Is Better: Sales Excellence Through Practice | Denis Champagne on SellMeThisPen PodAbout the episode:In this episode, Michael and Denis dive into the evolution of sales practices across three decades. They discuss why personalization requires understanding both seller motivations and buyer challenges, the importance of maintaining phone conversations in a digital world, and why building character through resilience matters more than pure sales skills for developing successful reps.About the guest:Denis Champagne is a seasoned sales coach and consultant who has spent over three decades in the trenches, from his early days selling furniture appointments as a teenager to managing...
2025-07-3140 minSellMeThisPen podcast#40 Change Management: Why Comfort is the Enemy of Growth | Nate Joseph on SellMeThisPen PodAbout 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...
2025-07-3139 minSellMeThisPen podcast#39 Why Sellers Must Master Buyer Enablement in 2025 and Beyond | Gal Aga on SellMeThisPen PodAbout 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...
2025-07-3141 minSellMeThisPen podcast#38 How to Customize Coaching to Enable Sales Teams for Success | Chris Nashed on SellMeThisPen PodAbout 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...
2025-07-3153 minSellMeThisPen podcast#37 How We Used AI to Scale Sales Training and Close Deals Faster | Pablo Jaramillo on SellMeThisPen PodAbout 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...
2025-07-3146 minSellMeThisPen podcast#36 How 1-on-1s Build High-Performing Sales Teams | Yusuf Ongel on SellMeThisPen PodAbout 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...
2025-07-3146 minSellMeThisPen podcast#35 How a Good SKO Can Upskill Your Sales Team | Ashton Williams on SellMeThisPen PodAbout 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...
2025-07-3144 minSellMeThisPen podcast#34 Sales Onboarding: From Retail to Tech - Lessons Learned | Jocelle Sarenpa on SellMeThisPen PodAbout 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...
2025-07-3145 minSellMeThisPen podcast#33 Reinforcement Strategies for Long-Term Sales Learning | Jay Shephard on SellmeThisPen PodAbout 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...
2025-07-3136 minSellMeThisPen podcast#32 What Companies Get Wrong About Internal Promotions | Eric Stavola on SellMeThisPen PodAbout 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...
2025-07-3147 minSellMeThisPen podcast#31 How To Run Successful Sales Role-Plays | Hamish Knox on SellMeThisPen PodAbout 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...
2025-07-3143 minSellMeThisPen podcast#30 The Science Behind Perfect Sales 1-on-1s: A VP's Guide | Jackelyn Skudra on SellMeThisPen PodAbout the episode:In this episode, Michael and Jackelyn dive into the art of effective sales coaching. They explore how building trust and asking the right questions trump telling answers, why coaching managers need more development than reps, and what it takes to create coaching sessions that drive both skill growth and mindset shifts.About the guest:Jackelyn Skudra has been in sales for over 20 years, starting as an individual contributor before moving into leadership roles, and now serves as VP of Sales at Xello. With a background in teaching...
2025-07-3140 minSellMeThisPen podcast#29 The Proven System That Creates Resilient Sales Teams | Brian Looney on SelMeThisPen PodAbout the episode:In this episode, Michael and Brian dive into building resilient sales teams through coaching, exploring why continuous feedback matters more than one-off training sessions. They discuss how effective coaching requires understanding individual motivations, the importance of leading by example rather than authority, and why partnering with product teams can amplify coaching success across the organization.About the guest:Brian Looney is a 20+ year sales veteran who's worn every hat in revenue organizations, from individual contributor to founder and CRO, with deep expertise in SaaS and intellectual property...
2025-07-3145 minSellMeThisPen podcast#28 Why Most Founders Fail With Sales Agencies | Amir Reiter on SellMeThisPenPodAbout the episode:In this episode, Michael and Amir dive into the realities of working with sales agencies and marketplace dynamics. They explore why companies should embrace both in-house and agency talent, how to set realistic expectations when hiring agencies and why being specific about your business challenges matters more than generic lead generation promises.About the guest:Amir Reiter is a seasoned sales leader and entrepreneur who built his career from door-to-door sales to leading CloudTask, a marketplace connecting companies with revenue agencies, software, and talent. With experience selling...
2025-07-3123 minSellMeThisPen podcast#27 From Door-to-Door to Enterprise: How Sales Training Really Works | Ryan Ing on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Ryan dive into how different companies approach sales training, from door-to-door at Vivint to enterprise at IBM. They explore why structured training programs work differently at companies of various sizes, and share insights on transitioning from founder-led sales to building scalable sales teams.About the guest:Ryan Ing has grown from selling door-to-door at Vivint to leading sales at tech giants like IBM, Oracle, and Shopify, along with helping several startups like Superlink and Tempo Labs build their sales functions. He's now...
2025-07-3134 minSellMeThisPen podcast#26 How to Build A High-Performance Learning Culture | Chris Bondarenko on SellMeThisPen PodAbout the episode:In this episode, Michael and Chris dive into everboarding and the importance of continuous learning in sales teams. They explore why having a strong enablement culture is crucial for revenue growth, how AI can accelerate learning programs, and Chris shares candid stories about leadership mistakes that shaped his approach to building high-performing sales teams.About the guest:Chris Bondarenko is a seasoned revenue leader with extensive experience leading teams as VP of Sales and now CRO of North America at 360Learning, where he champions the importance of...
2025-07-3134 minSellMeThisPen podcast#25 Building Champion Sales Teams with High-Touch Onboarding | Neman Syed on SellMeThisPen PodAbout the episode:In this episode, Michael and Neman dive into the essentials of high-touch onboarding programs in enterprise sales, breaking down why personalization and structured learning are crucial for new hire success. They explore how treating enablement as a competitive edge through detailed onboarding plans and role-specific training can transform new hires into trusted advisors, even in resource-constrained environments.About the guest:Neman Syed is a seasoned L&D professional, who previously led enterprise training at BlackBerry before joining MATRIXX Software as Sales Enablement Manager, where he now drives...
2025-07-3040 minSellMeThisPen podcast#24 Transform Your Sales Training: The Everboarding Revolution | Brooke Bachesta on SellMeThisPen PodAbout the episode:In this episode, Michael and Brooke dive into the concept of Everboarding and why traditional onboarding isn't cutting it anymore. They explore how continuous learning programs can transform sales enablement, break down common misalignments between enablement teams and sales leaders, and discuss practical ways to create engaging training that actually sticks with sales teams.About the guest:Brooke Bachesta is a dynamic enablement leader who started as an SDR, moved into management, and led enablement at brands like Outreach before becoming the Director of Learning Design at...
2025-07-3033 minSellMeThisPen podcast#23 Building High-Impact Enablement Teams | Adriana Romero on SellMeThisPen PodAbout the episode:In this episode, Michael and Adriana dive into the unique challenges of leading engineering enablement after transitioning from sales teams. They explore how measuring impact differs between technical and revenue teams, the importance of letting people fail safely, and why enablement leaders should encourage their teams to be proactively curious about the functions they support.About the guest:Adriana Romero is a seasoned enablement leader who transitioned from engineering to sales and now leads engineering enablement at OpenText, where she manages a team of eight supporting over 7,000...
2025-07-3037 minSellMeThisPen podcast#22 The Strategic Way to Roll Out Sales Methodologies | Michelle Curtis on SellMeThisPen PodAbout the episode:In this episode, Michael and Michelle dive into the realities of rolling out sales methodologies in enterprise organizations. They discuss why getting stakeholder buy-in is crucial before implementation, how to blend new methodologies with existing processes, and why keeping customer experience at the center of methodology choices leads to better outcomes.About the guest:Michelle Curtis is an enablement leader with extensive experience in education and sales, currently serving as the Director of GTC Programs at Polaris and participating in multiple enablement communities such as Revenue Enablement...
2025-07-3020 minSellMeThisPen podcast#21 Why Enablement Alignment is crucial for GTM Business | Nicole Ward on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Nicole dive into the realities of go-to-market team alignment and the crucial role of enablement in driving organizational success. They discuss why enablement should be the central force behind cross-functional initiatives, from SKO planning to CRM optimization, and share practical insights on building effective partnerships across marketing, RevOps, and sales teams.About the guest:Nicole Ward is a revenue enablement leader with over 15 years of experience across financial services, telecommunications, enterprise SaaS, and HCM industries, recently recognized as the Enablement Leader of...
2025-07-3032 minSellMeThisPen podcast#20 How To Drive Alignment and Innovation in Revenue Teams | Jon Fraser on SellMeThisPen PodAbout the episode:In this episode, Michael and Jon dive into the challenges of building alignment between sales, marketing, and CS teams. They explore why unified metrics and data hygiene matter, how to effectively manage tool adoption, and why both leadership involvement and cross-team compensation plans are crucial for breaking down organizational silos.About the guest:Jon Fraser is a senior revenue executive currently serving as the Chief Growth Officer at Dasro Tech Talent. Jon has a robust background in leading growth initiatives globally, with prior roles at Omniconvert and...
2025-07-3031 minSellMeThisPen podcast#19 Sales Coaching: Why Your Team Isn't Improving | Gordon Crane on SellMeThisPen PodAbout the episode:In this episode, Michael and Gordon dive into the realities of effective sales coaching and personal resilience. They explore why truly understanding each rep's unique motivations matters more than one-size-fits-all approaches, how small wins compound into bigger success, and share raw insights about bouncing back after setbacks in today's challenging tech landscape.About the guest:Gordon Crane is a seasoned sales leader with over 15 years of experience across companies like Avalara and Propel, bringing a unique perspective from his background in restaurant management and passion for coaching...
2025-07-3031 minSellMeThisPen podcast#18 How Competitive Enablement Saves You From Losing Deals | Hermann Handa on SellMeThisPen PodAbout the episode:In this episode, Michael and Hermann dive into the realities of competitive enablement in sales. They explore why focusing on key competitors is crucial for win rates, how to build effective sales messaging without bashing competition, and which coaching steps are essential for getting reps battle-ready in competitive markets.About the guest:Hermann Handa is a seasoned sales effectiveness and enablement leader with extensive experience across software companies like Oracle and Eloqua, now serving as Director of Sales Effectiveness at FCT and a founding member of Revenue...
2025-07-3032 minSellMeThisPen podcast#17 Building SDR Resilience: Learn More From Losses Than Wins | Andy Gillies on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Andy dive into building resilience through coaching, drawing from Andy's unique journey from acting to sales leadership. They explore why emotional intelligence and consistency are crucial for sales success, and how managers can create psychological safety while helping teams develop the right mindset to thrive.About the guest:Andy Gillies brings his unique background from acting to his current role as BDR Director at 8x8, having worked with notable companies like TechTarget and RingCentral. He leverages his theatrical experience to drive success...
2025-07-3036 minSellMeThisPen podcast#16 Mental Health in Sales: From Burnout to Peak Performance | Gayle Charach on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Gayle dive into the critical role of mental fitness in sales performance and leadership. They explore how building resilience through daily mental practices can transform productivity, discussing practical exercises to manage overwhelm and unlock creativity beyond just data-driven approaches.About the guest:Gayle is a veteran sales enablement professional with over 20 years of experience who pivoted to resilience coaching after experiencing burnout, joining the Positive Intelligence program to help sales leaders and teams achieve peak performance through mental fitness training. Following her...
2025-07-3045 minSellMeThisPen podcast#15 Blueprint to Run High-Impact Sales 1-on-1 Coaching Sessions | Nikki Schanzer on SellMeThisPen PodAbout the episode:In this episode, Michael and Nikki dive into transforming 1-on-1 coaching through the power of choice-driven conversations and effective frameworks. They explore common coaching pitfalls, ways to build genuine curiosity, measuring coaching effectiveness, and how to create safe spaces for team role-plays using the Two By Two framework.About the guest:Nikki Schanzer is a seasoned sales enablement leader who spent 10 years in sales before transitioning to post-sale operations, and then to enablement where she first started coaching reps and later leaders. She has extensive experience enabling...
2025-07-3038 minSellMeThisPen podcast#14 Building Resilience in Sales to Turn Failures Into Biggest Wins | Mike D'Angelo on SellMeThisPen PodAbout the episode:In this episode, Michael and Mike D'Angelo dive into building resilience in sales through effective coaching. They explore why survival mode often works against us, how to turn setbacks into opportunities, and Mike shares his practical frameworks for helping teams bounce forward instead of just bouncing back.About the guest:Mike D'Angelo is a seasoned sales leader and enablement expert with over 30 years of experience across enterprise tech companies like Highspot, MindTickle, Microsoft, and more, along with several startups. Recently, Mike shifted his focus to people enablement...
2025-07-3040 minSellMeThisPen podcast#13 From Auth0 to Okta: How Roleplays Got 90% of Reps to Hit Quota | Taylor Jurgens on SellMethisPen PodAbout the episode:In this episode, Michael and Taylor dive into the world of sales role-plays and scaling enablement programs. They explore why role-plays are crucial for sales success and share impressive results from Auth0: 90%+ reps hitting quota, 4% turnover rate, 60-day full ramp time, 90-day average sales cycle, and reps closing their first deals within 6 weeks. They discuss scaling challenges (from 20 to 160+ reps per bootcamp) and how AI could transform traditional training methods.About the guest:Taylor Jurgens has been in the trenches for a very long time. He started...
2025-07-3049 minSellMeThisPen podcast#12 The AI Revolution in GTM Teams: You Need to Catch Up NOW | Coach K on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Coach K (Jonathan Kvarfordt) dive into the practical realities of AI in sales teams. They break down the most valuable AI use cases for revenue teams - from automated data entry to sales simulations - and explore how finding the right balance between AI capabilities and human connection will shape the future of buyer-seller relationships.About the guest:Jonathan (Coach K) Kvarfordt is a veteran sales enablement professional and coach with over 15 years of experience, specializing in AI-driven sales strategies across startups...
2025-07-3046 minSellMeThisPen podcast#11 The Everboarding Blueprint to Transform SDR/BDR Teams | Jake Hollis on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Jake dive into the reality of building high-performing BDR teams through everboarding. They discuss why continuous learning beats one-off training, how to adapt to new tools without burning out your team, and Jake's approach to transforming cold calls by selling conversations instead of products.About the guest:Jake Hollis has been in the trenches crushing quotas, starting as an individual contributor and leading SDR teams to massive success for over a decade. He is currently a Senior Account Development Manager at OpenText...
2025-07-3039 minSellMeThisPen podcast#10 How to Get Enablement Buy-In from Sales Teams | Jared Balzer on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Jared discuss building effective partnerships between enablement and frontline managers. They explore why early collaboration is crucial for success, how to get buy-in from high-performing teams, and why enablement needs to be more than just a checkbox exercise.About the guest:Jared Balzer has a wealth of experience in sales, leadership, and enablement. He has built enablement programs at companies like Grubhub, Inspectorio, and many others.Where to find Jared:LinkedIn: https://www.linkedin.com...
2025-07-3031 minSellMeThisPen podcast#9 AI Productivity and Enablement: The Future of Work | Alexander Matyushenko on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Alex dive into how AI is transforming the workplace and why it's similar to past industrial revolutions. They explore why investing in employee upskilling beats replacement, how to measure AI implementation success, and share practical frameworks for leaders to drive technological adoption while maintaining human value.About the guest:Alexander Matyushenko is leading Sales Enablement and Productivity in America for Google Cloud, where he supports Google Cloud's growth by making thousands of Googlers competent, confident, and productive. Previously, he led Sales Productivity...
2025-07-2546 minSellMeThisPen podcast#8 The Truth About Toxic Sales Leadership And How It Kills ARR | Darren Hall on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Darren dive into the real talk about toxic leadership in sales and why 'no a-hole policies' are often the biggest lie in SaaS. They explore how toxic environments crush team performance, why fear-based management fails, and what it really takes to create psychological safety for reps to thrive through vulnerability and authentic leadership.About the guest:Darren is a powerhouse in the SaaS startup world. He’s led sales for several fast-growing companies like Avalara, Coupa, Oomnitza, and HiveMQ. His superpower lies in...
2025-07-2541 minSellMeThisPen podcast#7 AI in Sales Enablement: From Resistance to Results | Roderick Jefferson on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Roderick dive into the real talk about AI in sales enablement. They explore why embracing AI is crucial for modern sales teams, how to smartly leverage it across your go-to-market teams, and why AI should be treated just like a productivity tool to work smarter, not harder.About the guest:Roderick Jefferson is a globally recognized expert in sales enablement, a bestselling author of Sales Enablement 3.0, and a keynote speaker who has captivated audiences at major conferences like Dreamforce, the Sales Enablement...
2025-07-2530 minSellMeThisPen podcast#6 How to Align Sales Reps, Frontline Managers & Enablement | Nicole Plant on SellMeTHisPen PodcastAbout the episode:In this episode, Michael and Nicole dive into the realities of sales enablement and management alignment. They discuss reasons why misalignment happens, practical ways to build rep buy-in, get manager alignment, and measure enablement ROI beyond just training numbers.About the guest:Nicole Plant has been on both sides: BDR leadership and Enablement. She has helped some amazing brands like Loopio, Float, and now Relay build high-performing BDR teams.Where to find Nicole:LinkedIn: https://www.linkedin.com/in/nicole-plant/
2025-07-2529 minSellMeThisPen podcast#5 How to Implement AI for 15,000 Sales Reps | Ivan Pozgaj on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Ivan dive into the realities of implementing AI for large enterprise orgs. They discuss why consulting sellers before buying AI tools is crucial, how to avoid costly implementation mistakes, and why a data-driven approach beats gut feelings.About the guest:Ivan Pozgaj is a former elite hockey player with over 15 years of sales experience, primarily in Enterprise Sales. Recently, he transitioned into a Sales Enablement Program Manager role, focusing on innovation and in-flow of work at large organizations like Cisco.
2025-07-2536 min
SellMeThisPen podcast#4 Secrets to Nailing Your Sales Methodology Rollout | Stephanie White on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Stephanie discuss the evolution of sales methodologies, the importance of aligning them with company culture, and why successful implementation requires a partnership approach across teams.About the guest:Stephanie White is a Senior Director of Sales Enablement in tech and the founder of Enablement Reimagine. She's been recognized as a two-time one to watch and a winner of the Legend 23 award.Where to find Stephanie White:LinkedIn https://www.linkedin.com/in/stephanie-white-sales/
2025-06-2741 min
SellMeThisPen podcast#3 When HOW you sell is your only advantage | Graeme Pitches on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Graeme chat about how to sell when you don’t have flashy features to fall back on. They break down why how you sell is often more important than what you’re selling, especially in competitive markets. Graeme shares some cool stories from his time as a fuel trader and how those lessons shaped his approach to tech sales and enablement.About the guest:Graeme Pitches is a Sales Enablement Leader who started his career as a fuel trader, where he learned how...
2025-06-2736 min
SellMeThisPen podcast#2 Sales Methodologies Overhyped? | Ben Stokes on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Ben chat about upskilling sales teams, how sales methodologies are often overhyped, and why focusing on the basics might be the real key. They also talk about finding those ‘wow moments’ with buyers and making the whole process way simpler and more effective.About the guest:Ben Stokes is a seasoned VP of Sales. He's been building high performing teams for companies like ProofPoint and AdvancedMD. And now he is the VP of Sales at Responsive and the CEO of ForgePRO.
2025-06-2748 min
SellMeThisPen podcast#1 Sales Onboarding Gone Wrong: Common Mistakes | Andy Korenak on SellMeThisPen PodcastAbout the episode:In this episode, Michael and Andy talk about the common mistakes companies make during the sales onboarding process, the pressure it puts on new hires, and how to create a more effective and supportive environment for sales teams.About the guest:Andy has over 20 years of experience leading enablement for notable companies like Oracle, Impact, and 8x8. Now, he's the founder of MVP Sales Coach, where he offers expert sales coaching and fractional leadership, particularly beneficial for mid-sized companies.Where to find...
2025-06-2630 min