From Managing Partner to Chief of Staff

As a managing partner, I had to make tough calls with limited information while balancing strategic vision with financial realities. That kind of leadership thrives in ambiguity—it requires making decisions under pressure, aligning stakeholders, and executing without a guaranteed outcome.

It’s also much easier to see this now that my managing partner days are over and the last eight years are in the rearview mirror. When you’re in it, you don’t stop to label what you’re doing—you’re just making the best call you can with what you have. But looking back, I realize that this exact skill set—the ability to own decisions, move forward without perfect data, and keep an organization aligned—makes a great chief of staff.

The chief of staff role has long been a staple in government, but it’s still finding its shape in business. There’s no one-size-fits-all route into the position, but if you ask McKinsey, most chiefs of staff come from consulting, finance, or strategy backgrounds.

That’s why people tend to be surprised when I tell them I’m moving from 15 years as a founder/operator into a chief of staff role. They assume the best chief of staff candidates are the ones who’ve spent their careers advising executives—not the ones who’ve been executives themselves.

I confirmed this on a call with Vannin Chief of Staff, who mentioned that a new trend is emerging: more former founders and operators, like me, are stepping into these roles post exit. It makes sense. If the chief of staff is the bridge between vision and execution, then who is better than a founder who has built, scaled, and led an organization firsthand?

The McChrystal Group backs this up, describing the chief of staff as a strategic partner who ensures the leadership team’s vision translates into execution. And if that’s the job, founders with an exit have already been training for it—without even realizing it.

Think about it:

Most chiefs of staff facilitate strategic discussions. Former business owners? We’ve already made those decisions, carried their weight, and adjusted when things didn’t go according to plan.

There’s a difference between advising on tough decisions and owning the outcome. As a managing partner and founder/operator, I had to navigate complex challenges where hesitation wasn’t an option—every decision, big or small, carried weight.

Those lessons weren’t just about running a business. They were about leading with conviction in high-stakes environments, and they make me an asset in the chief of staff role.

As a managing partner, I had to make high-stakes decisions—hiring, pricing, partnerships—without perfect data. (There was never perfect data.) I learned that delaying too long could be as costly as moving too fast.

As chief of staff, executives don’t need someone to present options—they need someone who can cut through complexity, assess risk, and make a call. Having been in that position myself, I know how to balance strategy with decisive action and intuition.

Sometimes, I had to choose between making an investment that could fuel future growth or holding onto cash to protect the business. Sometimes, I got it right, and sometimes, I didn’t.

That’s real-world financial strategy.

Most chief of staff candidates know finance in theory. I know it from owning a P&L and living with the consequences of every decision. And that firsthand experience is invaluable when working with leadership on budgeting, forecasting, and long-term planning.

I’ve sat across from a new hire, full of promise, only to realize within 30 days that they weren’t the right fit. I’ve also felt the magic—and relief—of hiring someone whose dedication and alignment transformed the business.

A chief of staff serves as a key sounding board for leadership teams when making critical hiring decisions. Having been in the position of hiring, firing, and shaping company culture, I know firsthand that it’s not just about filling roles—it’s about building a team of aligned, high-performing individuals who can execute at the highest level.

As a managing partner, my job was to grow the business, drive success, and—most importantly—ensure its survival. I’ve always believed that the best leaders focus on impact, not credit.

That’s exactly the mindset required for a chief of staff. It’s not about personal recognition; it’s about making sure the CEO and leadership team have what they need to operate at their best. That’s where I thrive—working behind the scenes to make sure the right things get done by the right people at the right time.

Most chiefs of staff facilitate strategic conversations. However, former business owners have firsthand experience making high-stakes decisions and living with the consequences. This unique background sets us apart.

As a managing partner, I learned to make decisions, manage risk, and align strategy with execution. Running a business also taught me how to operate in ambiguity, drive teams forward, and execute with precision. These skills are not just useful—they are the foundation of an effective chief of staff.

That’s why former business owners are uniquely positioned to excel in this role. While most chief of staff candidates understand strategy, few have made the tough decisions determining success or failure.

This experience doesn’t just make the transition logical—it makes it a competitive advantage.