Thumbtack’s Larry Roseman Is 1 of the Best Leaders of the Year. His Top Advice

Larry Roseman knows it’s OK to showcase vulnerability on the job. That might sound like a leadership platitude, but as the 51-year-old CFO of Thumbtack, an app that links people in need of household repairs with skilled laborers, Roseman says there have been plenty of times when he was fine admitting that he was wrong or made a mistake. 

Since joining Thumbtack in 2020, Roseman has helped the gig-economy app quadruple its annual revenue and head count. He’s also helped the company raise $450 million in both debt and equity investments over the past four years. For the 2024 Best in Business package, Inc. spoke to Roseman about how humility—among other things—can be a hallmark of effective leadership.

Sam Blum: If I were to ask the people working under you “What makes Larry Roseman a great leader?” what do you think they’d say? 

Larry Roseman: Three key things I think about and try to embody when it comes to good leadership is to be vulnerable, be authentic, and meet people where they are. You’ve probably heard this saying of “Don’t let them see you sweat.” I think you should let them see you sweat. When you’re vulnerable, and put yourself out there, you build trust with your team.

OK, but what does that mean in practice? 

It’s taking responsibility when you don’t know something, or when you screw up. There’s an example that happened this year where two of my teams were not agreeing on something. I had a hand in creating that disconnect. When you raise your hand and say, “Look, I screwed up, this is my bad,” people are encouraged to do the same. It’s a way of saying “I messed up. Let’s figure it out and move forward.” 

Can you talk to me at all about how the business at Thumbtack has grown and succeeded since you came on board?

I joined in 2020 and since then we’ve 4X’d head count and revenue. We’ve taken the business from burning cash and being unprofitable to Ebitda positive and free cash flow positive. So we’re a profitable, growing business. I’ve grown my team from a handful of people—we were about five people when I joined—to more than 45 people at this point. 

What did you learn from the best bosses you had earlier in your career? How do you instill those lessons in your team today? 

One of the things that stuck with me is, at a certain point in your career, it’s not just about the numbers. It’s really about emotional intelligence and how you interact with peers, with your teams. It’s really about the people and influence, and that’s how you sort of get stuff done.

What leadership tactic has been essential to Thumbtack’s success? 

One of the things that I think makes a great leader is hiring people who are better than you at the things that you’re asking them to do. I always want to hire people who are subject matter experts, better than I am in whatever it is they do—whether it’s hiring a tax person or a controller. That way I can empower them to do their jobs.

What’s one piece of advice you would offer to entrepreneurs who want to grow their companies in 2025?

Over the past few years, we’ve been in an environment where companies were very focused on profitability. Companies were increasingly utilizing the Rule of 40 where a point of growth is worth the same as a point of profitability. In 2025, I think the pendulum will swing back toward driving growth. Companies and founders should be mindful that growth will again be rewarded with a premium valuation. This doesn’t mean that we are going back to growth at all costs, but founders and companies should take a balanced approach to growth versus profitability. It is a great feeling when you control your destiny because you are growing profitably.