Coach2Scale: How Modern Leaders Build A Coaching Culture

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,...

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 th...

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 quest...

Every sales leader has heard the mantra: “Pipeline cures all.” But what if that’s only half the truth? In this episode, Matt Carey, SVP of Global Sales at FIS, breaks down why more pipeline isn’t always the answer— the right pipeline is. He shares hard-earned lessons from leading sales teams at Oracle, SAP, and FIS, explaining how top-performing organizations prioritize quality over quantity, meas...

Performance improvement plans (PIPs) are meant to help struggling reps, but more often than not, they’re just a step toward the exit. So why do they fail? And what should CROs and frontline sales managers do instead to truly develop their teams? Why does urgency hurt your coaching? In this episode of Coach2Scale , host Matt Benelli sits down with Eric Hachmer and Steve Frappier of High Five Adviso...

Too many sales teams operate on instinct, hoping charisma and hustle will carry them to quota. However, Paul Fannon, Global CRO at Bottom Line, views sales as a science. In this Coach to Scale episode, Paul explains why a structured, data-driven approach is the key to predictable success. He shares how top reps aren’t necessarily the most talented—they’re the most disciplined. You’ll hear why work...

Sales leadership is full of hidden pitfalls that can derail even the most experienced managers. In this episode, Kevin Gaither—former ZipRecruiter sales leader, CRO of Inside Sales Expert, and author of It Happened on the Sales Floor —pulls back the curtain on the most common mistakes sales managers make. He challenges the myth that you can be friends with your reps, shares the six must-have trait...

Most sales leaders focus on hitting their numbers, but few take the time to diagnose why their teams struggle in the first place. In this episode, Bob Tharp, a seasoned sales leader with 35+ years in complex solution sales, reveals the hidden obstacles that stall revenue growth and how CROs can fix them. From controlling the controllables to holding reps accountable without micromanaging, Bob shar...

Thad Zilka, a veteran leader in sales and leadership, discusses the transformative power of coaching in sales performance. Drawing insightful parallels to the world of sports, Thad challenges the notion that star salespeople don't need guidance. Through sharing his own journey, he highlights the pivotal role of structured business plans and the consistent need for accountability to truly achieve g...

What if the secret to transforming your sales team lies within the art of the one-on-one meeting? Join me, Matt Benelli, and our special guest, Andy White, VP of Sales at Trivy, as we debunk myths and uncover these meetings' critical role in building trust and alignment in modern sales teams. We dive into the heart of creating coaching cultures and learn why remote and hybrid work environments mak...

Can senior executives really afford to skip coaching? Join us for a fascinating discussion with Josh Horstmann, Operating Partner at Francisco Partners Consulting, as we dismantle the myth that top leaders don't need coaching. We promise you'll learn how to harness coaching for all levels of performance, from struggling team members to high-flying stars like UFC champion Jon Jones. Josh shares uni...

Unlock the secrets to skyrocketing your sales growth with insights from Brent Holloway, the CRO and co-founder of SaaS Sales Advisors. Imagine doubling your company's revenue without expanding your sales force—Brent breaks down how understanding unit economics and refining customer profiles are key to achieving this. We navigate through the intricate layers of sales productivity and efficiency, un...

Unlock the secrets of genuine connection in sales and leadership with our guest Lane Monson, an executive leader and coach who challenges the conventional wisdom of salesmanship. Do most salespeople really know how to connect deeply with others? Discover what Lane has to say as we unravel the five levels of connection, which many sales professionals only partially navigate. Through Lane's insightf...

What if sales success wasn’t just about the money? Join us as we challenge this age-old myth with insights from Jim Gannon, SVP of Sales at Sysdig. Discover how autonomy, competition, and a genuine drive to impact the business play pivotal roles in achieving sales excellence. Jim reveals why curiosity and the willingness to learn from peers set top performers apart, shedding light on the motivatio...

What if the secret to exceptional coaching lies not in having all the answers, but in embracing authenticity and vulnerability? Join us as we chat with Chris Michelmore, the head of mid-market acquisition at Zoom, who brings his unique perspective on coaching both athletes and salespeople. Chris challenges the notion that great coaches must be the best performers, instead highlighting the power of...

As we close the book on 2024, I want to take a moment to say THANK YOU. Whether you tuned in for one episode or all 52, you're part of a movement that believes coaching is the rocket fuel for performance. This year, Coach the Scale recorded over 65 episodes , reaching thousands of sales leaders. But this isn’t about vanity metrics—this is about impact. Each episode brought lessons that slapped us...

What if your beliefs about feedback and coaching timelines are holding you back? Guest host Colum Lundt, CEO of CoachEm, takes the helm to interview our regular host, Matt Benelli! Both are co-founders of CoachEm and share the myths and misconceptions about coaching sales teams. Matt dismantles the notion that coaching yields immediate results, likening this misconception to expecting instant mast...

What if everything you thought you knew about leadership was turned on its head? Join us for an enlightening conversation with J.D. Sillion, a two-time CEO and three-time CRO, as he dissects the myths surrounding leadership and unveils a powerful framework for guiding teams through both high-growth and turnaround situations. Drawing inspiration from sports legends like Phil Jackson, J.D. emphasize...

Keith Rabkin, the Chief Revenue Officer at PandaDoc, takes us on a journey through his unconventional path to sales leadership, revealing a fresh perspective on motivating sales teams that challenges the age-old myth of money being the sole motivator. Keith unpacks the art of understanding individual aspirations and leveraging them to enhance performance through his innovative two-by-three matrix...

In today’s episode, Matt interviews Ed Diller, Sales Leader at New Relic. They explore effective coaching practices and myths in sales leadership. They discuss the importance of strategic communication, creating win-win scenarios, and maintaining work-life balance in a post-COVID world. Ed shares valuable lessons from his extensive career, emphasizing the need for risk-taking, clear communication,...

Today, Matt discusses the significance of building coaching cultures with sales leader Derek Bates, VP of Northeast Sales at Alteryx. They delve into the myths of sales coaching, the importance of efficiency and work-life balance, and Derek's unique 3-P (People, Process, Performance) framework. Derek shares insights from his extensive career at Oracle and how he has applied those experiences at Al...

In this episode of Coach2Scale, Matt Benelli sits down with Mark Roberge, the founding CRO of HubSpot and the Co-Founder of Stage2 Capital. They discuss innovative approaches to sales coaching, including the importance of focusing on the percentage of reps hitting quota and why new reps should not shadow top performers. Mark shares insights on proactive coaching methods and the significance of dat...

In this episode of Coach2Scale, Matt speaks with Pat Deskin, Chief Revenue Officer at NewStore, to debunk the myth that senior sales reps don't need coaching. Pat emphasizes the importance of consistent one-on-ones, urgency in sales, and the integration of people and process to scale companies successfully. The discussion also explores Pat's influential experiences and favorite coaching philosophi...

In this episode of Coach2Scale, Matt Benelli engages in a thought-provoking conversation with Jill Harris, VP of Sales for North America at GoTo. Jill shares her insight on balancing empathy and accountability in sales coaching. She emphasizes the importance of asking the right questions and fostering a collaborative environment when it comes to sales leadership. Jill introduces her Sales Coaching...

Today host Matt Benelli engages in a thought-provoking conversation with sales leader Steve Boss. The discussion spans a variety of topics, including effective sales coaching, the challenges of transitioning to management, and the importance of self-advocacy and mentorship. Highlighting the significance of managing both up and down within an organization, the episode provides practical advice on b...