Dropbox, Inc. announced a significant leadership change, naming Ross Tennenbaum, the president of tax compliance software firm Avalara, as its new Chief Financial Officer.
The appointment,, marks a strategic hire as the cloud storage company navigates a revenue dip and sharpens its focus on artificial intelligence.
Tennenbaum will succeed Tim Regan, who has decided to resign after more than five years as CFO and nearly a decade with the company. Dropbox emphasized in a securities filing that Regan’s departure was not due to any disagreement on company strategy or operations, but rather his desire to pursue the next chapter of his career.
Financial Acumen for a New Chapter
Dropbox CEO Drew Houston welcomed the new executive, stating, “Ross brings a strong combination of financial acumen, operational experience, and deep knowledge of the tech landscape, and I’m excited to partner with him as we navigate our next chapter.”
Tennenbaum, 47, joins at a pivotal time. Last month, Dropbox reported a slight year-over-year revenue decline of 0.7% for Q3 2025, with total sales of $634.4 million. The company also saw a drop in paying users, from 18.24 million to 18.07 million. Outgoing CFO Regan attributed part of the revenue pressure to the wind-down of FormSwift, a document workflow business acquired in 2022.
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Compensation and Broader Leadership Reshuffle
According to an SEC filing, Tennenbaum will receive an annual base salary of $550,000 and a one-time cash signing bonus of $350,000. He brings over two decades of finance and operations experience, including nearly ten years at Avalara where he served as CFO before becoming president. His background also includes a decade in investment banking at Goldman Sachs and Credit Suisse.
The CFO transition is part of a broader leadership update. Dropbox simultaneously announced the appointment of Eric Webster, an operating partner at Silversmith Capital Partners, as its new Chief Business Officer.
Strategic Pivot to AI and Core Products
In a blog post, the company linked these changes to its strategic priorities: “These changes come as we deepen our focus on scaling Dropbox Dash and strengthening our core file storage and sync experience.” Dash is the company’s AI-powered universal search tool, highlighted by Regan as a key priority for scaling in the upcoming fiscal year.
A Fond Farewel
Dropbox paid tribute to the departing Regan, praising him as a “steady and trusted leader” who guided the company through its IPO in 2018 and strengthened its financial foundation. “Tim supported our teams with humility, integrity and the best sense of humor,” the company stated.
As Tennenbaum prepares to step into the role, the market will be watching to see how his expertise in scaling tech firms will help steer Dropbox through its current transition and toward its AI-driven ambitions.
