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.