What happens when a founder-led sales strategy hits its limits? In this episode of Coach to Scale, Ken Grosso, 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.
What happens when the founder who sold the first $2M in ARR becomes the biggest obstacle to growth?
That’s the tension we unpacked in our latest episode of Coach to Scale with Ken Grasso, veteran CRO, former Adobe exec, advisor to growth-stage founders, and now the force behind Catalyst Peak Ventures. If you’re a CRO who’s been handed the keys to a founder-led rocket ship or a founder listening in, this episode is a roadmap for transforming chaos into confidence through process, leadership, and mindset.
Here are the lessons that hit hardest, and why they matter now more than ever.
1. Founder-Led Selling Is Not a Strategy, It’s a Phase
Ken has sat in both seats: founder and sales leader. He’s seen the passion, the scrappiness, and yes the “happy ears” that come from believing every enthusiastic demo turns into a deal. But as Ken reminds us, instinct isn’t a strategy.
What founders do well is sell with conviction and urgency, which is rarely scalable. CROs must step in not to replace that energy, but to translate it into repeatable motion. That means building systems, not personas.
Coach’s Note: If the founder is still the best seller in year three, you don’t have a sales engine you have a single point of failure.
2. Top Reps Don’t Automatically Become Top Managers
It’s a myth as old as the quota: promote your best rep, and they’ll lead the team to glory.
Ken shuts that down. Leadership is a different sport. It requires pattern recognition, emotional intelligence, and a deep commitment to the system not just personal performance. He urges CROs to hire (and coach) leaders who are builders, not just closers.
Coach’s Note: Don’t mistake individual excellence for team potential. Coach for systems, not heroics.
3. Process Is the Playbook, Not the Punishment
Sales process isn’t bureaucracy, it’s your best quarterback. It gives you visibility into the field, helps you call the right plays, and keeps your team moving downfield with purpose.
Ken leans on sports analogies (which I obviously love) to make the point: would you drop a top college QB into a broken NFL system and expect greatness? No. But CROs do it to new hires all the time.
A well-built process sets expectations, reduces ramp time, and builds confidence from rep to boardroom. It’s what enables coaching, not what replaces it.
4. You Can’t Scale What You Can’t Teach
One of the biggest takeaways from Ken’s journey is this: if your selling model isn’t teachable, it’s not scalable. That’s why CROs must work with founders to extract tribal knowledge and turn it into onboarding, enablement, and operating rhythm.
That’s also where many sales leaders struggle; they fail to “sell the system” internally. Ken talks about the need for CROs to educate and build trust with founders, reframing their role from disruptor to multiplier.
Coach’s Note: Translate founder vision into frontline execution. That’s the CRO superpower.
5. Be Ready for Your Own Pivot
In a deeply personal moment, Ken talked about his own career evolution, leaving Adobe, entering the executive job market, and confronting the realities that many senior leaders face today: ageism, assumptions, and a shifting hiring landscape.
His solution? Plan B is You. He spun up his own advisory firm, leaned into fractional leadership, and started writing the playbook for others to do the same.
CROs: take note. The market changes. Titles expire. But skills, relationships, and systems thinking endure.
Final Whistle: Don’t Wait for the Pain
Ken’s parting advice to founders and CROs alike was this: don’t wait until you’re out of time or out of cash to fix your sales process.
A broken GTM system won’t just stall growth, it will kill valuation. Whether you’re gearing for investment or acquisition, your ability to predict, coach, and scale revenue matters more than any single deal.
🎧 Listen to the full episode:
“From Founder Chaos to Sales Confidence” on Coach to Scale, available now on Apple, Spotify, and YouTube.
➡️ Listen now at coachem.io
