You can read, seek advice, and study the playbook. But nothing truly prepares you for the pressure of being a PE-backed CEO until you’ve sat in the chair. 

Few know that pressure better than Ascend alumnus Tom Waitt, former turnaround CEO of a private equity-backed e-commerce business and current CFO in a PE portfolio company. Tom came up through finance, but his first CEO experience taught him that PE executive leadership isn’t just about financial management. It’s about people, culture, and the courage to lead through uncertainty.

Tom’s story is one of grit, humility, and growth. We sat down to talk about what he learned from his first time in the CEO chair.

Dan Cremons: In 2023, you stepped into the CEO role for the first time in a tough spot. It was a founder-led business facing post-COVID headwinds and supply chain issues. Take us into the moment: what did those early days feel like?

Tom Waitt: Chaos, honestly. It was a turnaround, and I did what most first-time CEOs do: I gravitated to what I knew. Coming from a finance background, I went straight to the numbers: inventory, margins, cash flow. That felt like solid ground to find my footing on. 

I realized we had real inventory and cash flow issues that I had to address quickly. On my second day, the lender came in for a field audit, and I quickly realized how little visibility we had into inventory. We couldn’t say confidently what was in the warehouse. So I gathered everyone — even office staff — and said, 'We’re all staying until we count every item in the warehouse.' We were there until 2:00 in the morning, sweating, counting, trying to get our arms around the inventory problem. 

Dan: That must have been a wakeup call for the team. 

Tom: It was. But I quickly realized the job wasn’t just about fixing the inventory or financial issues. It was about leading people through the fog. There was no way to get through these early cash flow issues unless I could create clarity for the team on what was important to focus on, why, and how we’ll work through it together. I quickly learned that you can’t spreadsheet your way out of issues like this.

Dan: What was the biggest surprise once you were in the chair?

Tom: How much of the job is about people and culture. I completely underestimated that. 

I thought: if we just bring structure, discipline, and some good financial rigor, things will fall into place. And make no mistake, those things were important. But I realized along the way that people need a reason to believe. They need to feel part of a bigger story to buy into the changes we had to make. 

In retrospect, I waited too long to realign the team on our values and vision. If I were doing it again, I’d start there. I’d get the leadership team in a room and say, “Who are we now, and who do we want to be?” I realized it’s really tough to change the business until you change the mindsets and behaviors that drive the business. 

Also, it took me too long to realize that the culture had been created in the founder’s image. Once he stepped out, that glue disappeared. People didn’t have a shared sense of direction anymore. I thought implementing process and structure would fill the gap, but it didn’t. You can’t drive a turnaround purely on logic. You have to win hearts and minds.

Dan: You were an East Coast finance guy walking into an outdoor e-commerce company full of outdoors people. How did you win them over?

Tom: (laughs) Yeah, I showed up day 1 in Lululemon khakis. I could see it on their faces. They didn’t think I’d last two weeks. And honestly, they weren’t wrong to question it. I didn’t look like them, I didn’t talk like them, and I didn’t understand their world. 

But I tried. I remember one distinct turning point moment: I went on a hunt with a few people on my team one weekend early in my tenure. I had no idea what I was doing. They probably thought I’d shoot myself in the foot. But it showed them I cared enough to try. They realized I wasn’t just some PE guy who could do spreadsheets. I wanted to understand their world. That’s when trust started to build.

I learned not to underestimate the power of small investments in the relationships with your team. 

Dan: Speaking of relationships, a lot of first-time CEOs struggle with the loneliness of the job. Did you feel any of that?

Tom: Absolutely. You think you’ve got support, and technically you do. You’ve got your board, your investors, your team. But no one else really knows what it’s like to have that weight on your shoulders. 

I had a friendly board, but I didn’t lean on them like I should have. I was too afraid of looking like I didn’t know what I was doing. I didn't let myself be vulnerable with them. I wasn’t as proactive about seeking their guidance and tapping into their wisdom.

I now understand: the board’s not there to judge you. They’re there to help you think. They want you to be successful. I got some good advice from them early on, but I wish I’d been more open and proactive about seeking their advice throughout the turnaround. 

Dan: You mentioned advice you got from your board early on. Tell me about that.

Tom: Yeah. Before I started, my boss (our lead board member) said, “Look, you’re going to mess things up.” (laughs) I was like, “Thanks for the confidence boost!” But he didn’t mean it in a bad way. He meant: you’re going to make mistakes, and that’s okay. It’s to be expected for a first-time CEO. 

I fought that lesson so hard at first. I wanted to prove I could get it all right. But that fear of failure and self-imposed pressure to get everything right slowed me down. I made slower and less confident decisions. 

If I could go back, I’d tell myself: take big swings sooner, fail fast, learn, and pivot. That’s how you grow.

Dan: What were the areas where you hesitated?

Tom: There were two big things I hesitated on: some important personnel decisions, and pivoting the business to focus on our own products. I knew both were necessary, but fear of failure and indecision delayed those calls. 

In hindsight, I should have followed my instincts more confidently. You learn that being decisive doesn’t mean being reckless. It means making the best call you can with the data you have, and then being prepared to adapt if you need to. 

Dan: That’s a great point — making decisions faster, even with imperfect data. How has that impacted your approach to leadership now? 

Tom: After that experience, I realized one of the biggest blockers for first-time CEOs is waiting for perfect data and information. Hate to break it to you, but if that’s your bar, you’ll be waiting a while. Nevertheless, getting adequate data is still important to making high-quality decisions. 

I think it was Jeff Bezos who said that most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being way to slow.

But in some of these companies, getting to even 70% is a tall order. In many small and mid-sized companies, the systems and dashboards are woefully underdeveloped. To that end, I’ve started building a small data and analytics function at our firm that can go in and help give our operators better visibility faster… so they can make better decisions faster.  

Dan: What did the experience change for you as a leader overall?

Tom: It made me see leadership differently. I’m back in a port-co CFO role now, and I’m a way better CFO because of this experience. 

I can anticipate what my CEO needs before they ask. I think about how decisions affect the whole enterprise, not just my finance function. Sitting in the CEO chair forces you to see the business from a higher altitude. It forces you to think about value creation broadly, not just the financial components. Once you’ve seen the business from this vantage point, you can’t unsee it. It changes how you show up in every role after that.

Dan: Any final words of advice to other first-time CEOs out there?

Tom: Don’t try to do it alone. It’s easy to think you have to prove yourself or that showing weakness will make people lose confidence in you. But that fear of looking like I didn’t know what I was doing actually held me back.

Also, winning the hearts and minds of people and building trust is arguably the most important thing you can do early on in your tenure. If you can’t do this, everything else is at risk. So don’t underinvest in the relationships, and make sure people are clear on what you’re playing for.