• Coach2Scale: How Modern Leaders Build A Coaching Culture

  • By: CoachEm
  • Podcast

Coach2Scale: How Modern Leaders Build A Coaching Culture

By: CoachEm
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  • Summary

  • Welcome to Coach2Scale - How Modern Leaders Build Coaching Cultures Join Host Matt Benelli for conversations with management professionals in B2B companies who share the belief that effective coaching improves the performance of every team member. Our mission is to help leaders become better coaches. Coach to Scale is sponsored by CoachEm, the world's first AI coaching execution platform that leverages evidence-based coaching to increase quota attainment.
    CoachEm
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Economics Marketing Marketing & Sales
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Episodes
  • The CRO Aligning with Capital Strategy with Michael Janes | Coach2Scale Episode #87

    The CRO Aligning with Capital Strategy with Michael Janes | Coach2Scale Episode #87
    Apr 15 2025

    In this conversation of Coach the Scale, host Matt Benelli sits down with Michael Janes, CRO, investor, and co-founder of Rapid Commercialization Partners, to explore why top sales leaders are shifting their focus upstream. Janes unpacks his core philosophy: Sell to the strategy behind the capital, revealing how understanding a company’s ownership structure, whether private equity, venture-backed, or founder-led, can dramatically reshape how reps position value, influence internal champions, and align with executive priorities.

    From myth-busting the idea that activity volume alone drives results to challenging how most one-on-ones miss the mark, Janes offers a grounded yet forward-looking perspective on what it takes to lead high-performance sales organizations. Listeners will walk away with practical insights on coaching beyond the forecast, the dangers of “super rep” management, and why the real leverage often starts at the board level, not the buying committee. If you’re a CRO or sales leader aiming to uplevel your team and shorten the path to influence, this conversation is required listening.

    Key Takeaways:
    1. Sell to the strategy behind the capital
    Don’t just “follow the money”—understand the investor’s goals and align your sales motion to how capital is deployed, managed, and expected to grow.

    2. Coaching needs to shift from deal review to skill development
    Most one-on-ones are ineffective because they focus on forecasting instead of developing the behaviors that lead to consistent performance.

    3. One-on-ones are broken when they lack preparation and structure
    Great coaching starts with preparation; otherwise, reps get a therapy session or a pipeline interrogation, not actual development.

    4. Sales managers are overwhelmed and under-equipped
    FLMs are juggling too many priorities with little training on how to coach or drive rep performance—this gap undermines quota attainment.

    5. Activity without purpose is a myth that needs killing
    The old-school mindset of “just make more calls” misses the point; consistency only matters if it’s paired with relevance and precision.

    6. Start high and cascade down—not the other way around
    The most strategic salespeople begin with senior-level conversations, understanding investor priorities, then work downward to shape the internal sale.

    7. Internal champions are built through strategic guidance, not feature pitching.
    Could you make sure to provide your buyers with the narrative they need to sell internally by aligning your message with capital goals and business outcomes?

    8. Overlay roles only work when they add real value
    Janes proved that overlays focused on investor relations can be a force multiplier—but only if they help reps access decision-makers and frame deals through a capital lens.

    9. Respect the chain of command—but don’t ask permission
    When engaging PE or VC boards, it's critical to keep execs in the loop without letting them gatekeep the conversation.

    10. Managers need enablement, too—not just reps
    The assumption that great reps make great managers is flawed; without systems, training, and coaching support, FLMs can’t scale performance across the team.

    Ways to Tune In:
    Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A
    Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434
    Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU
    Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77
    Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703
    YouTube: https://www.youtube.com/@Coach2Scale
    CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward. These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.

    Learn more at coachem.io
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    48 mins
  • Blind Spots and Broken Systems with Kevin McCarthy | Coach2Scale Episode #86

    Blind Spots and Broken Systems with Kevin McCarthy | Coach2Scale Episode #86
    Apr 8 2025
    In this episode, bestselling author and CEO of Blind Spots, Kevin McCarthy, shares a deeply personal story of how unchecked blind spots, not bad intent, can quietly derail careers, culture, and company performance. After spending 33 months in federal prison for a white-collar crime he didn’t knowingly commit, Kevin emerged with a mission: help leaders see what they’re not seeing before it costs them everything.When top performers become first-line managers, most are handed the title without the tools. We explore why so many sales managers default to deal reviews instead of skill development, how perception gaps fracture team trust, and why most coaching is misnamed and misdirected. Kevin breaks down the cognitive science behind decision-making under pressure and explains how poor coaching hygiene is driving regrettable attrition. This conversation hits directly at the heart of today’s frontline execution crisis and offers a clear path forward for CROs who want to scale with integrity.Top Takeaways: Blind spots—not bad intentions—derail leaders. Kevin’s story underscores that well-meaning leaders can still make costly mistakes if they lack self-awareness and critical thinking under pressure.Perception gaps destroy trust and performance. The difference between how a manager intends to communicate and how it's received can lead to misalignment, demotivation, and attrition.Sales managers are promoted, not prepared. High-performing reps are often elevated into management without training in people leadership, coaching skills, or emotional intelligence.Most sales coaching isn’t actually coaching. Managers default to forecasting and deal reviews, missing the opportunity to develop reps’ skills in a systematic and personalized way.One-size-fits-all management breaks teams. Kevin explains how failing to adapt your coaching style to each rep’s communication style and mindset leads to disengagement.The hardest job in the company is being ignored. First-line managers juggle execution, admin, and development but rarely get the support, tools, or training to coach effectively.Reps leave when they don’t feel developed. Talent walks when managers only talk numbers. Real coaching connects with reps’ goals, strengths, and growth trajectory.Self-awareness is the most underdeveloped leadership skill. Kevin makes the case that improving self-awareness and emotional intelligence in managers is the single best lever for improving sales culture.Frontline execution problems are strategic risks. What looks like a rep issue is often a management system failure—CROs must prioritize manager enablement if they want predictable performance.Ways to Tune In:Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 YouTube: https://www.youtube.com/@Coach2Scale CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward. These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.Learn more at coachem.io
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    1 hr and 6 mins
  • Stop Telling, Start Coaching with Mike Montague | Coach2Scale Episode #85

    Stop Telling, Start Coaching with Mike Montague | Coach2Scale Episode #85
    Apr 1 2025
    Matt Benelli sits down with Mike Montague, sales and marketing expert at Avenue9 and host of the Human-First AI Marketing podcast, for a candid conversation about what sales managers are still getting wrong about coaching. From the myth that leaders need to have all the answers to the burnout caused by "super reps" turned managers, Mike breaks down why most 1:1s fail and how asking better questions can flip the script on team performance. If you're still equating pipeline reviews with coaching, this one’s for you.They also unpack the critical gap between coaching and execution and why online learning and conversation intelligence tools fall short without behavior change. Mike shares his "Iron Man vs. Terminator" analogy to help sales leaders reframe their use of AI and makes the case for exposure therapy and tough love as the missing ingredients in most sales organizations. Whether you’re trying to scale performance or stop regrettable attrition, this episode gives frontline and senior leaders a roadmap for more effective, accountable teams.Top Takeaways:Coaching is about asking questions, not giving answers. Managers who try to “know it all” become bottlenecks; real coaching empowers reps to think for themselves.The best leaders make themselves irrelevant. Like elite sports coaches, great sales leaders build systems and skills so teams can operate independently.AI won’t replace salespeople, but it will replace those who don’t use it. Sales leaders need to think like Ironman, using AI as an enhancement tool to increase awareness and execution, not as a replacement for human strategy.The frontline sales manager (FLM) role is the hardest in the company. FLMs are overwhelmed by tasks, undertrained in coaching, and lack the time or tools to develop their teams effectively.Selling someone what they need and can afford isn’t cheating—it’s your job. Sales should focus on qualified buyers with budget, authority, and urgency, not on convincing disinterested prospects.Coaching fails when it focuses only on deals, not skills. Most coaching sessions are just pipeline reviews; they don’t address the behaviors that improve performance in the long term.Exposure therapy is essential for growth. Managers need more reps, not more theory, to improve at hard conversations or high-stakes moments.Online learning is helpful but only if it’s paired with feedback and behavior change. Asynchronous learning tools often reinforce what reps already know; without coaching moments, they don’t close performance gaps.Managers who need approval frequently avoid necessary conversations. Leadership requires discomfort, and effective managers must overcome the urge to be liked to hold reps accountable.Coaching is different from managing—and most people don’t know how to do it. There's a widespread misunderstanding of coaching; most FLMs were never taught how to develop others, and it shows.Ways to Tune In:Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77 Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703 YouTube: https://www.youtube.com/@Coach2Scale CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward. These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.Learn more at coachem.io
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    53 mins
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