Welcome to Episode 100 of the Coach2Scale Podcast! In this milestone edition, host Matt Benelli delivers a no-nonsense Q2 debrief packed with hard-earned lessons, powerful guest stories, and leadership truths that cut through the noise. From blind spots that sink careers to the non-negotiables of trust, culture, and coaching, this episode distills what it really takes to scale teams and drive meaningful results. Hear firsthand from Kevin McCarthy on self-inflicted downfall, from John Walston on building mental resilience, and from Neil Wood on solving, not selling, your way to a billion-dollar success.

This episode is more than a recap; it’s a call to action. Matt shares five brutally honest themes that every sales leader, coach, and executive needs to hear: coaching is about asking questions, not issuing commands; culture is defined by what you tolerate, not what you say; inconsistency erodes trust; and enablement isn’t optional; it’s your competitive edge. Whether you're leading a team or trying to level up, this episode will challenge your assumptions and light a fire under your Q3 game plan. Let’s get after it, and as always, CoachEm if you want to keep ‘em.

Key Takeaways

1. Adversity Doesn’t Build Character; It Exposes It
2. Stop Pitching. Start Solving. Or Step Aside.
3. Coaching Is a Skill; And Most Managers Suck At It
4. Culture Isn’t a Slogan; It’s What You Tolerate

Guests
1. Kevin McCarthy - https://www.linkedin.com/in/kevinmccarthycsp/
2. John Walston- https://www.linkedin.com/in/john-walston-63a042206/
3. Neil Wood - ⁨https://www.linkedin.com/in/neilwoodconsulting/
4. Michael Muhlfelder - https://www.linkedin.com/in/mikemuhlfelder/
5. Tom Young - https://www.linkedin.com/in/tom-young-7aba11/
6. Mike Montague - https://www.linkedin.com/in/mikedmontague/
7. Jeff Keplar - https://www.linkedin.com/in/jeffrey-keplar-63a2b86/
8. Mark Kosoglow - https://www.linkedin.com/in/mkosoglow/
9. Kevin Gaither - ⁨https://www.linkedin.com/in/kevingaither/
10. Tony Burnside - https://www.linkedin.com/in/tonyburnside/
11. Pam Dake - https://www.linkedin.com/in/pamela-dake-1152483/

What happens when a founder-led sales strategy hits its limits? In this episode of Coach to Scale, Ken Grasso, veteran CRO, advisor, and founder of Catalyst Peak Ventures, pulls back the curtain on the messy, mission-critical transition from instinct-driven selling to structured, scalable revenue operations. With experience leading global go-to-market teams and helping companies grow from zero to IPO, Ken shares unfiltered insights on why founders often struggle to let go of sales, the costly myth of the “natural-born” sales leader, and how process, not personality, is the real growth engine.

Packed with real talk for CROs, revenue leaders, and founders alike, this conversation explores the pivotal role of coaching cultures, how to hire for system-fit over resume flash, and the urgent need to professionalize sales before seeking investment or exit. You’ll also hear Ken’s candid reflections on career reinvention, building credibility as a fractional exec, and why planning for the next chapter before you need to is essential for long-term impact. Whether you’re scaling your first team or rethinking what makes sales truly sustainable, this episode is a playbook in disguise.

Top Takeaways

1. Founder-led selling becomes a liability as you scale
Early-stage founders may be the best sellers at first, but their instinctive, unstructured style can block repeatability and growth.

2. Great sales reps don’t automatically make great managers
Promoting top performers without leadership skills or process discipline can stall team performance and create chaos.

3. The sales process is the foundation, not a nice-to-have
A defined, teachable sales process enables forecastable growth, efficient onboarding, and higher valuations.

4. CROs must earn trust and re-educate founders on go-to-market
Transitioning founder-led orgs to scalable operations requires a blend of credibility, patience, and strategic coaching.

5. Hiring should prioritize system-fit and coachability.
The best candidates align with your GTM model and are eager to operate within a defined system, not just shine as individual contributors.

6. You can’t outrun a broken foundation with short-term wins
Heroics might save a quarter, but without an operational structure, you’ll eventually burn out or break the model.

7. Fractional leadership can unlock massive value for growth-stage teams
Bringing in experienced operators part-time can help companies avoid costly misfires and build maturity without overextending budgets.

8. Plan your career pivot before the market makes you do it
Ken urges seasoned leaders to proactively define their “Plan B,” emphasizing personal reinvention and long-term career resilience.

9. Strong systems beat star power—ask the NFL.
Drawing on sports analogies, Ken explains why team performance relies more on consistent playbooks than flashy individuals.

10. Valuation depends on your GTM maturity.
Investors and acquirers don’t just buy your product they buy your ability to sell it repeatedly, predictably, and without founder involvement

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 hard decisions CROs and sales leaders must make to scale performance without sacrificing culture. You'll hear why conviction matters more than consensus, how to spot reps ready for more than just promotion, and why internal networks can fast-track productivity. If you’re tired of recycling the same top 10% and ready to build a coaching culture where every position matters, this conversation will shift how you lead.

Top Takeaways

1. Don't fear reassigning key accounts.
Even top performers can adapt; keeping all the best accounts with senior reps creates a revolving door for new hires and stalls team growth.

2. Break the “greenfield trap” for new reps.
Reps in undeveloped territories often fail not from lack of talent, but from poor territory design and lack of enablement.

3. Promotion isn’t leadership readiness.
Great reps often struggle as managers unless they’re taught how to coach, hold people accountable, and operate strategically.

4. Coaching must go beyond deal reviews.
Most managers default to pipeline triage; real coaching means developing skills that affect every deal, not just the current quarter.

5. Internal networks matter as much as external ones.
High-performing reps build relationships across legal, finance, and other internal teams early, compressing ramp time and increasing deal velocity.

6. The best leaders make ideas that help the business, not themselves.
Dan’s biggest promotions came from pitching business-first ideas with no personal gain attached; conviction creates opportunity.

7. Equitable territories create stronger teams.
Giving everyone a real shot at success, rather than over-rewarding tenure, builds momentum and reduces attrition.

8. Friendship and accountability can coexist.
Strong relationships within the team don’t weaken performance; they create the trust needed for tough conversations and high standards.

9. Ask: Are you making the news or reporting it?
Reps who lead the sales process proactively outperform those who simply react to buyer-driven next steps.

10. You can build momentum and hit the number.
It’s not either-or; with the right structure, you can build long-term capability while executing in the short term.

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 culture builder.

This episode is a must-listen for CROs, VPs of Sales, and frontline managers navigating burnout, underperformance, or high turnover. You’ll walk away with tactical ways to shift from transactional management to human-centered leadership, without sacrificing accountability. Topics include managing anxiety in high-pressure environments, turning 1:1s into developmental moments, and why “get over it” is the fastest way to lose trust and performance. If you lead teams, this conversation will challenge how you measure success and show how culture is a quota strategy.

Takeaways
1. “Just stop it” doesn’t work, especially in sales leadership.
Telling someone to push through stress or anxiety without support not only fails, but it also damages trust and culture.

2. You can’t lead people effectively if you don’t understand what they’re carrying.
Empathy isn’t a soft skill; it’s a leadership multiplier that directly impacts motivation and consistency.

3. Physical movement drives mental clarity and performance.
Exercise helped Walston recover from a personal crisis, and research shows it’s as effective as medication for many mental health issues.

4. Positivity isn’t the same as being happy.
Leaders can model resilience by moving forward with optimism, even while acknowledging discomfort or hardship.

5. Your team won’t grow if your 1:1s are just pipeline inspections.
Coaching conversations should go beyond deal reviews to include skill development and personal connection.

6. Culture is built in the moments between numbers.
Asking your reps about their weekend and remembering what they said builds trust that translates into accountability.

7. Positive self-talk is a skill leaders must model and teach.
Verbalizing functional thoughts (especially out loud) has a 10x psychological effect compared to internal dialogue.

8. Gratitude changes how you lead and how people follow.
Being grateful for struggle, not just outcomes, shifts the mindset and allows leaders to better support their teams.

9. Even one moment of connection can shift someone’s trajectory.
Whether it’s a smile, a T-shirt slogan, or a question at the right time, leaders have the power to influence more than they realize.

10. “Easy is not best,” and your reps need to hear that.
High standards, not hand-holding, are what help people rise. But they must be delivered with belief and support.

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 with your sales reps?”

Moderated by Matt Benelli, host of the Coach to Scale podcast, this unscripted, no-holds-barred session dives into real stories, polarizing philosophies, and battle-tested experiences on the fine line between empathy and authority.

What you'll learn:

When friendship enhances performance, and when it kills accountability

Why sales managers struggle with tough conversations

The hidden career risks of blurred boundaries

How modern leaders navigate connection, trust, and coaching culture

Get actionable takeaways for building high-performing sales teams while balancing trust, professionalism, and results.

This is not your average webinar. It’s honest. It’s engaging. It’s real sales talk for real sales leaders.

Sponsored by CoachEm: The world’s first AI coaching execution platform, built to scale sales success through data, coaching, and culture.

COMMENT below: Can you be friends with your reps? Where do YOU draw the line?

📥 Subscribe to the Coach to Scale podcast and never miss a real-world sales leadership discussion.

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, personalized coaching drives not just rep development but cross-functional alignment and executive trust.

Julie also dives into the frontline manager dilemma: they’re overwhelmed, under-supported, and often promoted without the tools to coach effectively. She offers actionable frameworks for feedback that sticks, one-on-ones that matter, and why even your top performers still need direction. Whether you’re a CRO trying to stabilize performance or a new manager navigating the leap from IC to leader, this episode delivers tactical guidance grounded in experience, not theory.

Top Takeaways

• Generic sales training fails high-context teams.
  Off-the-shelf training doesn’t stick when sales cycles are complex, technical, or regulated; coaching must be personalized to the rep’s world.
• Radical candor beats performance reviews.
  Feedback should be frequent, specific, and kind, not saved for annual reviews or buried in vague praise.
• High performers plateau without stretch coaching.
  Even your best reps need friction to grow; without it, they stagnate and disengage quietly.
• Effective 1:1s start with knowing the rep as a person.
  Understanding motivations, feedback styles, and personal goals unlocks performance in ways dashboards never will.
• Coaching isn't a calendar event; it’s a culture.
  Building feedback loops into day-to-day operations (like peer call reviews and structured office hours) creates sustained behavior change.
• Not all reps are ready for feedback in the same way.
  Great managers check in before delivering feedback to ensure the timing and delivery fit how each rep processes input.
• Manager consistency separates good teams from great ones.
  Sporadic coaching drives uneven results; systematized coaching practices help managers scale development across the team.
• First-line managers need coaching too.
  Most FLMs were promoted without being taught how to lead; equipping them is the fastest way to impact rep performance and retention.
• Team-first leaders earn executive trust.
  Julie’s “Team Number One” mindset shows how customer success leaders can earn CRO alignment by focusing on business outcomes, not just function-specific wins.
• Customer centricity must be operationalized.
  Declaring CS as a priority isn’t enough; Julie made it real by embedding it into cross-functional KPIs and role-specific accountability.

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, not outdated, and how the caricature of the “golf-playing rep” is holding companies back from serious revenue performance.

This episode is a must-listen for CROs, VPs, and FLMs navigating the blurred lines between coaching, leadership, and execution. Jeff unpacks what makes a sales leader worth following, why frontline managers often fail (and how to fix it), and how real coaching, not just pipeline reviews, builds resilient teams. From scaling at Oracle to advising modern startups, Jeff shares lessons that cut through the noise and help leaders build teams that win the right way.

Key Takeaways
1. Leadership isn’t granted by title, it’s earned in the field
Sales managers gain real influence by showing up with their team, facing the same pressure, and modeling accountability, not by hiding behind their job title.

2. Sales-led growth isn’t outdated, it’s just misunderstood.
Many critics confuse poor execution with obsolescence; in reality, complex sales still require human insight, coaching, and influence that product-led strategies alone can’t deliver.

3. Stop promoting 'super reps' and expecting them to be great managers
The skill set that drives individual performance often lacks what’s needed to coach, develop, and retain a team, especially in high-growth or enterprise contexts.

4. Great sales leaders don’t kiss up and kick down, they build teams that follow them anywhere
The mark of strong leadership is not upward politics but whether former team members would choose to work with you again.

5. Salespeople need coaching beyond the deal.
Too many 1:1s are just pipeline checks; true coaching focuses on skills, behaviors, and long-term development that compound over time.

6. In enterprise sales, the product doesn’t close the deal; people do
Unlike self-serve SaaS tools, enterprise software buyers need trust, consultation, and risk mitigation that only a well-prepared rep can deliver.

7. When reps are treated like resources, they leave
High attrition often traces back to poor or absent development; reps stay when they feel seen, supported, and challenged.

8. Managers must be the rep’s advocate, even when it costs political capital
Defending your team when it's hard is the kind of leadership people remember and rally around, especially in performance management decisions.

9. Friendship and leadership aren’t mutually exclusive.
While being “one of the crew” can backfire, relationships built on trust and mutual respect lead to better coaching conversations and loyalty.

10. Coaching is influence, not control.
The goal is to shape behavior through insight and conversation, not compliance, which is also what great selling looks like.

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 number, Mike says it’s time to wake up.

Listeners will learn why great reps don’t always make great leaders, how to use the “Four W’s” to qualify real opportunities, and why many teams are scaling mediocrity with automation. Mike also offers hard-won advice for CROs under boardroom pressure, and a stark reminder to protect your health and values as you chase performance. It’s part strategy, part therapy, and all signal, no noise.

Top Takeaways
1. Great salespeople don’t always make great sales leaders.
Mike challenges the myth that success as a rep naturally translates to leadership, emphasizing that leading a team requires a completely different skillset.

2. Stop promoting outsiders into sales leadership roles.
Bringing in non-sales professionals to run sales teams often fails because they lack the experiential knowledge and empathy to lead sellers effectively.

3. Sales is a profession and must be treated like one.
Like finance or engineering, sales requires continuous training, discipline, and a commitment to mastery, not just charisma or improvisation.

4. Outdated qualification methods like BANT hurt your deals.
BANT is adversarial and obsolete; it leads to mistrust and surface-level qualification instead of real discovery.

5. Use the ‘Four W’s’ to qualify deals more accurately.
Mike’s framework: What happened? Why now? Who owns the project? When do they need to be live? Creates human-centered, business-grounded qualification.

6. The pipeline problem is systemic, not just executional.
Teams rely on inflated pipelines and 4–5x coverage ratios because poor qualification and forecasting have become normalized.

7. Most sales tech stacks enable mediocrity at scale.
Without sound fundamentals, even the best tools just help teams do the wrong things faster.

8. Sales math still matters: maximize yield, minimize waste.
Effective revenue leaders think like manufacturers, optimizing the fewest inputs (leads) for the highest output (closed deals).

9. Salespeople must take ownership of their own development.
With unlimited learning resources available, Mike urges reps to stop waiting for enablement and start taking personal accountability.

10. CROs must prioritize clarity, courage, and communication.
From cleansing the pipeline to resetting board expectations, Mike says leadership means telling hard truths and doing the right thing even when it’s unpopular.

11. Burnout is real, and it’s not worth it.
He ends with a human message: no job is worth sacrificing your health, family, or identity, no matter how big the number.