Dropbox CFO Timothy Regan to Step Down After Five-Year Tenure

Dropbox announced Wednesday that longtime finance chief Timothy Regan will leave his role after five years as CFO. He will be succeeded by Ross Tennenbaum, currently a senior leader at tax software firm Avalara, as the file-hosting company continues to accelerate work on artificial intelligence products.

Shares of Dropbox slid more than 5% in morning trading following the leadership update.

Tennenbaum, who currently serves as president at Avalara and previously held its CFO role, will formally assume the CFO position at Dropbox on December 16. His arrival comes at a time when the company is directing more resources toward AI features, including Dropbox Dash, a tool designed to connect services such as Google Workspace and Slack to streamline file organization.

Regan joined Dropbox in 2016 as chief accounting officer and played a central role in the company’s 2018 initial public offering. He became CFO in 2020 and will remain with the company as a non-executive employee through March 15, 2026, ensuring a transition period as Tennenbaum steps into the role.

The San Francisco–based company reaffirmed that its fourth-quarter and full-year financial results remain on track with the guidance previously issued. Dropbox expects Q4 revenue between $623 million and $626 million on a constant-currency basis.

The company also lifted the midpoint of its 2025 annual revenue forecast by $18 million, now projecting a midpoint of $2.51 billion, compared with the prior midpoint of $2.49 billion.

Earlier this year, Half Moon Capital, an activist investor, urged Dropbox to eliminate its dual-class share structure, which grants CEO Drew Houston enhanced voting power. A spokesperson for the firm said it intends to continue discussions with Dropbox leadership once the current transitions conclude.

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