What happens when a top-performing rep becomes a people-first leader in one of the most demanding roles in tech? In this episode of Coach2Scale, Jeff Perry, CRO at Carta, shares his leadership journey from his early days at Oracle to building high-performing, diverse teams at Carta. He unpacks the misconceptions that still hold sales leaders back, like the idea that only hard-charging, deal-focused managers succeed, or that considerable company experience doesn’t translate to startup growth. Jeff challenges these myths with candor, offering lessons for anyone navigating their evolution as a leader.
The conversation tackles why being a “nice leader” isn’t a liability, how to hire from non-obvious backgrounds, and why no one should ever lose a deal alone. Matt and Jeff also dig into the most challenging job in sales, the frontline manager, and why equipping them with the right mindset and tools is the only way to scale performance sustainably. Whether you’re a rep, manager, or CRO, this episode will help you rethink how leadership, culture, and coaching intersect to drive lasting results.
Sales leadership isn’t about adopting someone else’s style. It’s about figuring out your own and having the courage to lead from it. That was the throughline in my recent conversation with Jeff Perry, CRO at Carta, on the latest episode of Coach2Scale. Jeff’s journey, from Oracle to DocuSign to Carta, offers a blueprint for how to build performance at scale by betting on people, not playbooks.
If you’re a CRO thinking about how to drive sustained growth without burning out your managers or cycling through reps, you’ll want to study this one closely. Jeff doesn’t just talk about leadership theory; he lives it in the pressure-cooker world of high-growth tech. Here are the most important takeaways from our conversation that every revenue leader should take to heart.
1. Don’t Inherit a Leadership Style. Build Your Own.
Jeff spent the first phase of his career learning how “big company” sales orgs operate but when it came time to lead at smaller, more agile companies, he didn’t shed that experience. He translated it. The myth that big company leaders can’t thrive in early-stage startups is outdated and lazy. What matters isn’t where you’ve been, it’s whether you know how to operate without the bureaucracy and win the trust of your team. Jeff made that transition by leaning into who he was not pretending to be who someone else wanted.
Key point: Your authenticity is an asset, not a liability. Leadership is more believable and more scalable when it’s real.
2. Being a “Nice” Leader Isn’t Weak. It’s Effective.
Another false narrative? That you can’t be empathetic and demanding at the same time. Jeff makes it clear: the best leaders are both. They hold the line on expectations but build the kind of trust that earns extra effort. His style isn’t command-and-control; it’s human and consistent. And in today’s market, consistency is currency.
If you want 212° effort from your people, you’d better earn it.
3. Team Balance > Lone Star Output
Here’s a scenario: Would you rather have a manager hit 130% of goal with just a few reps making quota, or finish at 115% with the whole team contributing? Jeff didn’t hesitate to give him the balanced team every time. Not only is it more sustainable, it’s a sign that the manager is coaching, developing, and creating an environment where performance is repeatable.
As CRO, this is where your eyes need to be: not just on the forecast, but on how the team is performing as a system.
4. Never Lose a Deal Alone
Top reps don’t go solo. They activate their network executives, product, and enablement, and they know when to pull in their CRO. Jeff wants his team to call him in. “If you’re not using me, I’m wondering why,” he said.
Sales is a team sport. Your job as CRO is to make that mindset standard. Individual brilliance might get the first deal. Collective execution gets the second, third, and fourth.
5. Your FLMs Are Drowning. Throw Them a Life Raft.
Jeff and I agreed: frontline managers have the toughest job in the org. They’re caught between the pressure of delivering the number and the expectation of coaching their team. Most default to the forecast. That’s not coaching, it’s triage.
If you want to build a true performance culture, you have to give FLMs the tools, time, and training to do their real job: developing people. Otherwise, you’ll keep getting deal reviews disguised as 1:1s and reps who never move past mediocrity.
6. Culture Is What You Tolerate, and What You Build
Jeff’s approach to diversity wasn’t performative. It was tactical. Diverse teams perform better, challenge groupthink, and reflect the customers they serve. But building that kind of team doesn’t happen by accident. It happens when leaders hire beyond résumés and prioritize inclusion as part of the performance equation.
If your leadership team looks too much like your past, don’t be surprised when you repeat it.
7. Coaching Is a Strategic Lever, Not a Soft Skill
One of the most important things Jeff shared: he didn’t get to where he is just because he hit his number. He got there because someone gave him a shot, invested in his development, and helped him see a path he didn’t even know existed.
He’s paying that forward, and it’s paying off. Carta’s growth isn’t just about product-market fit. It’s about people-market fit. And that starts with leadership that coaches the whole person, not just the pipeline.
Final Thought for CROs
If you’re trying to scale, but your managers are overwhelmed and your reps are stuck, it’s time to change the playbook. Start by listening to this episode. Then ask yourself: Are we building leaders who develop people or just promoting reps who know how to close?
Jeff Perry is proof that coaching culture scales. And that the best leadership doesn’t come from pretending to be someone else.
It comes from leaning in.
Listen to the full episode: “Leaning Into Who You Are to Lead”, now live on Coach2Scale
And remember coach ’em if you want to keep ’em.
