When the Silicon Valley Bank crisis erupted in early 2023, Larry Roseman was already well-acquainted with market upheaval. A member of the CFO class appointed around 2020—just as the pandemic began—Roseman had weathered previous storms. He began his career amid the dot-com collapse, then advanced through the 2008 financial crisis. “Scar tissue helps,” he tells us.
So when he landed in Palm Springs for a tennis tournament and learned SVB was in freefall—taking all of Thumbtack’s cash with it—his weekend plans were immediately sidelined. “Literally getting on the plane and landing, and the whole thing sort of blowing up,” Roseman recalls. “I was holed up in the hotel room for days,” working through how to ensure payroll and access to capital.
That crisis became a defining moment. “That was the catalyst for us,” he tells us. Roseman used it to pivot the business away from growth-at-all-costs and toward sustainable, profitable growth. In just a few years, Thumbtack went from -$60 million in EBITDA to +$60 million.
His ability to adapt comes from a varied career path—public accounting at Ernst & Young, investment banking at Bear Stearns and JPMorgan, and operational finance at eBay, where he helped spin off PayPal. At Thumbtack, a national home services marketplace, he’s scaled the finance team tenfold and implemented a discipline around contribution margin, hire rate, and CAC.
“The P&L doesn’t lie,” Roseman tells us—especially in times of crisis, when it’s clarity, not comfort, that defines the leader.
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CFOTL: Tell us about Thumbtack. What does the company do?
Roseman: If you’re not familiar with Thumbtack, we’re a marketplace business. We’re the most trusted way for homeowners to hire the right pro for their home repair and maintenance projects. We actively support customers from the beginning—diagnosing the problem—all the way to getting it done. We help them make confident decisions and ensure they get what they need completed.
That means matching the customer to the right pro and giving them the confidence to hire, knowing that Thumbtack has their back if something goes wrong. On the pro side, we deliver intentful, committed customers—we’re getting them jobs, not just leads. Our goal is to be the best investment they can make to grow their business.
We currently have 300,000 pros on the network, 4 million customers, and we operate in every county in the United States across 500 different categories. Ultimately, we’re a technology business focused on innovation.
What sets us apart is similar to what distinguishes any great marketplace—whether it’s eBay, Amazon, Uber, or DoorDash—it’s about matching both sides of the marketplace effectively and efficiently. For us, that’s the homeowner and the pro. You succeed when someone comes to you with a need and you can use technology to quickly and elegantly match them with the right solution.
One of our key metrics is the “hire rate,” or success rate—how often someone submits a request and actually gets their project fulfilled. That’s our holy grail—it sets us apart and helps build our competitive moat.
CFOTL: How is your FP&A team structured? Do team members rotate between different parts of the business?
Roseman: On the FP&A side, we’ve structured the team in two parts. First, we have a corporate FP&A team that focuses on the senior leadership team, the board, and external-facing work.
Then we have a business finance—or business FP&A—team. These are like mini CFOs, each partnered with a different business leader. For example, one is focused on the pro side, another on demand generation, and another on the product and engineering experiences we build. Each of those leaders has a dedicated finance partner to support them.
Thumbtack | www.thumbtack.com | San Francisco, CA