What happens when your top-performing rep becomes a struggling front-line manager? In this episode, Dan Freund, Chief Sales Officer at Invoice Cloud and former Oracle sales leader, unpacks the leadership gap plaguing high-growth sales orgs. From rethinking territory design to balancing equity with accountability, Dan shares how he transformed underperforming teams into consistent winners, without clinging to sales superstars or status quo assumptions. This episode offers a candid look at the har...
Jun 24, 2025•41 min•Ep. 98
When sales targets are missed, most leaders look at the pipeline, process, or personnel. But what if the real issue is a lack of psychological safety? In this episode of Coach to Scale, host Matt Benelli sits down with John Walston, author, entrepreneur, and founder of the Keep On Movement, to explore how vulnerability, empathy, and consistency in leadership can transform sales outcomes. Walston shares how personal adversity reshaped his leadership style, making him a more effective coach and cu...
Jun 17, 2025•37 min•Ep. 97
Can Sales Managers Be Friends with Their Reps? The Ultimate Sales Leadership Debate Should leaders be friendly or firm? In this epic live debate from CoachEm’s inaugural Closing Arguments series, two powerhouse sales veterans, Mark Kosoglow (Co-founder & CEO at Operator, former Outreach leader) and Kevin "KG" Gaither (CEO of InsideSalesExpert.com, former ZipRecruiter exec), go head-to-head on one of the most controversial questions in sales leadership: “Can, should, or would you be friends w...
Jun 10, 2025•56 min•Ep. 96
What happens when your strongest reps stop getting better? In this episode of Coach2Scale , Julie Fox, Global Director of Customer Success at Cin7, shares how she transformed "steady but stuck" team members into high-impact players. From busting the myth of one-size-fits-all sales training to implementing a radical feedback culture, Julie unpacks how coaching isn't just for underperformers. It’s a strategic growth engine for the whole team. She explains how her approach to structured, personaliz...
Jun 03, 2025•51 min•Ep. 95
Jeff Keplar, former sales executive at Oracle, MapR, and Google, joins Coach2Scale to challenge one of today’s loudest narratives in SaaS: that product-led growth has made traditional selling obsolete. In this candid, no-nonsense conversation with Matt Benelli, Jeff lays out why complex, high-stakes enterprise deals still demand skilled sellers, strong managers, and real leadership in the field, not just slick UX and freemium funnels. He explains why sales-led growth is often poorly executed, no...
May 27, 2025•57 min•Ep. 94
Matt Benelli sits down with sales veteran and Calm Ocean Sales founder Mike Muhlfelder for a no-BS conversation every CRO and sales leader needs to hear. With three decades of experience at companies like Oracle, IBM, and Jitterbit, Mike shares his unfiltered perspective on what’s gone wrong in modern B2B sales from bloated pipelines and broken qualification processes to tech stacks that mask, rather than solve, performance problems. If you’re relying on BANT and 4x pipeline math to hit your num...
May 20, 2025•47 min•Ep. 93
Sales enablement isn’t just a support function anymore; it’s a measurable, strategic driver of revenue growth. In this episode of Coach2Scale , Pam Dake, Senior Director of Go-To-Market Enablement at Menlo Security, shares how enablement must evolve from ad hoc product training into a disciplined, data-driven engine that shrinks sales cycles, improves pipeline velocity, and makes forecast calls more predictable. Pam challenges outdated views of enablement as an "art" form and shows why top organ...
May 13, 2025•54 min•Ep. 92
In this episode of Coach to Scale , sales trainer and former Olympic trials athlete Neil Wood joins Matt Bonelli to challenge one of the most pervasive mistakes CROs and sales leaders make: reserving coaching only for the bottom performers. Drawing from decades of real-world experience and high-performance athletics, Neil makes the case for why top sales reps need consistent, skill-based coaching just as much as, if not more than, struggling reps. From tactical strategies to improve frontline ma...
May 06, 2025•1 hr•Ep. 91
In this episode of Coach to Scale, we sit down with Tony Burnside, SVP of APJ at Netskope, to dismantle the outdated playbook on sales leadership. Tony challenges the myth that effective managers need to lead through pressure, fear, or control. Instead, he shares his approach to building high-performing, culturally aligned teams, starting with hiring good humans, creating space for accountability, and making coaching a non-negotiable part of the manager’s role. With over 200 reps across 15 count...
Apr 29, 2025•50 min•Ep. 90
Tom Young, VP of Sales at BMC Software, joins Matt Benelli to challenge outdated assumptions about how enterprise sales should work. Drawing on decades of experience and a recent moment on the other side of a buying decision, Tom reveals how sellers often leave buyers to navigate complex purchasing decisions alone, leading to stalled deals, weak adoption, and low rep confidence. The problem isn’t buyer intent. It’s a lack of structure, coaching, and guidance. This conversation gets tactical and ...
Apr 22, 2025•1 hr 3 min•Ep. 88
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...
Apr 15, 2025•48 min•Ep. 87
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...
Apr 08, 2025•1 hr 6 min•Ep. 86
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...
Apr 01, 2025•53 min•Ep. 85
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, measure pipeline health beyond raw coverage, and avoid common forecasting pitfalls. Matt also explores t...
Mar 25, 2025•49 min•Ep. 84
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 Advisory to uncover the biggest mistakes sales leaders make when it comes to coaching and accountability. ...
Mar 18, 2025•55 min•Ep. 83
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 ethic can’t be taught but can be uncovered, how sales leaders should adapt their coaching style to ...
Mar 11, 2025•47 min•Ep. 82
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 traits for every sales hire, and explains why most coaching efforts fall flat. If you’re a CRO or frontli...
Mar 04, 2025•1 hr 9 min•Ep. 81
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 shares a practical, no-nonsense approach to building a high-performing sales organization. Join host Mat...
Feb 25, 2025•53 min•Ep. 80
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 greatness. His perspective provides a refreshing look at how even seasoned professionals can benefit ...
Feb 18, 2025•41 min•Ep. 79
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 make these interactions more indispensable than ever. Andy shares his expertise aligning team and compa...
Feb 11, 2025•58 min•Ep. 78
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 unique insights on smarter hiring, building a "virtual bench," and creating a coaching-centric culture ...
Feb 04, 2025•44 min•Ep. 77
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, uncovering how tailored strategies can lead to consistent, sustainable success. Brent introduces us to...
Jan 28, 2025•45 min•Ep. 76
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 insightful anecdotes, including a transformative experience with a Navy chaplain, learn how asking the right...
Jan 21, 2025•54 min•Ep. 75
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 motivations that propel seasoned pros and ambitious newcomers alike. The episode further unpacks the essence ...
Jan 14, 2025•54 min•Ep. 74
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 meeting individuals where they are and guiding them toward their goals. Through compelling anecdote...
Jan 07, 2025•47 min•Ep. 73
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 in the face and whispered, "Pay attention." So, let's hit rewind on the top 10 lessons from 2024 tha...
Dec 24, 2024•7 min•Ep. 71
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 mastery in swimming. They advocate for feedback that strikes a balance, highlighting strengths while pin...
Dec 17, 2024•52 min•Ep. 70
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. emphasizes nurturing potential over wielding authority to foster an environment where teams can thrive. Our d...
Dec 10, 2024•54 min•Ep. 69
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 approach. With an emphasis on setting personal goals and addressing team development needs, Keith pr...
Dec 03, 2024•44 min•Ep. 68
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, and the benefits of focusing on strengths. He also highlights the role of coaching in career progre...
Nov 26, 2024•44 min•Ep. 67
