Why the Best Sales Leaders Say Yes First—Lessons from Carta's Jeff Perry

On our most recent episode of Revenue Mavericks, I sat down with Jeff Perry, Chief Revenue Officer at Carta.

He told me a story about sitting in his boss's office at Oracle, being asked to sign an NDA, and having absolutely no idea what was about to happen.

Was he getting fired? Promoted? Something else entirely?

He was managing database sales teams at the time. Things were going well. But Dan Freund, his boss, had pulled him aside for a conversation that started with legal paperwork - never a comfortable moment.

Then Dan told him: Oracle was planning to acquire Sun Microsystems. And he wanted Jeff to leave the database world he knew inside and out and help rebuild hardware sales teams from scratch.

Jeff's response? "I'm in."

No deliberation. No asking for time to think about it. Just yes.

Looking back, Jeff admits he was "young and naive" in that moment. He didn't have hardware experience. He had no idea what rebuilding sales teams at that scale would actually require. But someone he respected had opened a door, and Jeff had learned something playing college baseball that stuck with him: when you get tapped on the shoulder, you say yes.

1. Finding the Toughest Person in the Room

Jeff played baseball at Santa Clara University, which meant he'd gone from being a standout pitcher in high school to the bottom of a much smaller, much more competitive pyramid.

"You were sort of the big fish in the small pond in high school," he told me. "Then all of a sudden, you join a team of people who are much bigger and stronger than you, throw harder, have more experience. You bring yourself back down to the bottom rung."

His strategy was simple: find the person who scared him most and work to match their level.

That person was Bob Pilthorpe, a junior when Jeff was a freshman. "He was tough and he was mean, and I was scared of him. We were all scared of him as freshmen because he was so much bigger and developed and stronger. But he was mentally tough and had this burning will to win no matter what. I watched that, and I was like, I want to be like Bob."

Jeff carried that approach into his career. Find the best person. Watch what they do. Work harder to close the gap. It's the mentor model in its simplest form, and it works.

2. The Door That Changed Everything

Back to Dan Freund's office.

Jeff said yes to rebuilding hardware sales because he trusted the opportunity more than he feared the uncertainty. And that decision completely rewired his career.

"I would not be where I am now had Dan not given me that opportunity," Jeff said. "It helped me for my remaining years at Oracle. It helped me recognize that I wanted to move on and make a bigger impact in a smaller company. In my mind, it opened the door for me to get to Docusign. That then opened the doors for me to get to Carta."

One yes. Multiple doors.

Jeff's philosophy now: unless something smells terrible about an opportunity, raise your hand and say yes. Tackle it with the same effort and curiosity you'd bring to anything else. The worst case? It doesn't work out for a couple quarters and you find the next thing. And if you put in the work - if you do right by the business, the people, the company - the next thing will open up anyway.

He's confident about this because he's lived it. That single decision 15 years ago to leave his comfort zone taught him how to build organizations, not just manage them. Those skills are exactly what he needed when he joined Carta seven years ago as Chief Revenue Officer.

3. The Balance Nobody Talks About

When I asked Jeff about his framework for success, he didn't point to a process or a playbook. He pointed to something most revenue leaders think they have to choose between: operational rigor and human connection.

Jeff doesn't think you have to choose.

"There's how you run and manage the business: top of funnel, pipeline, conversion rates, all the operational mechanics. But there's also the people component. I feel like there's this balance to it. You can be both."

He's built his leadership style around getting close to people. Really close. Understanding what makes them tick. Making them feel like he's invested in their success, not just hitting the company number.

Some leaders avoid this because they worry it makes the hard conversations harder. Jeff's experienced the opposite.

"There are many days where we have hard conversations. The feedback I give or the things I ask them to do, they don't always like it. But at the core of it, they know I have the best interest of our team, our people, and our company in mind. We're in it together."

That connectivity doesn't weaken his ability to lead. It strengthens it. People invest more when they know their leader is genuinely invested in them.

What This Means for Revenue Leaders

Jeff's career isn't built on a single framework or a proprietary process. It's built on a series of decisions that most people would hesitate to make.

Say yes to the unclear opportunity. Find the best person and work to match them. Get close to your people and stay close, even when it's hard.

The revenue leaders who adopt this mindset build organizations where people raise their hands, take risks, and grow into roles they didn't know they were capable of. The ones who don't will keep losing talent to companies that understand leadership is operational excellence and human investment, not one or the other.

If you want to hear the full conversation, Jeff's episode is worth your time.