Dropbox announced the departure of CFO Timothy Regan, who has led the company’s finance function since 2020, and named Ross Tennenbaum, former president and CFO of Avalara, as his successor effective December 16, 2025.
Regan will remain with Dropbox as a non‑executive employee through March 15, 2026, receiving a $250,000 advisory fee to ensure a smooth transition. Tennenbaum will bring a decade of experience in tax‑software and investment banking, having served as Avalara’s president from April 2024 to December 2025 and as its CFO from 2020 to 2024.
The transition comes as Dropbox accelerates its investment in artificial intelligence, notably its AI‑driven product Dropbox Dash. Management believes Tennenbaum’s background in technology compliance and capital allocation will help steer the company’s growing AI initiatives while maintaining financial discipline.
Dropbox’s financial outlook for the fourth quarter and full year 2025 remains unchanged, with guidance that meets or exceeds the company’s November 6, 2025 forecast. The company’s leadership signals confidence that the new CFO will support continued profitability amid intensified AI spending.
Market reaction to the announcement was muted, with analysts noting that the CFO change reflects a routine succession plan rather than a strategic shift. Investors remain focused on how the new leadership will manage capital allocation for AI projects, but no immediate impact on the company’s valuation outlook was observed.
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