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Earlier this week, Dropbox announced that longtime CFO Timothy Regan will step down and be succeeded by Ross Tennenbaum, currently president and former CFO of tax software company Avalara, as the company accelerates investments in AI tools like Dropbox Dash, which connect services like Google Workspace and Slack.
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The leadership change puts a seasoned software finance executive at the center of Dropbox’s push to transform its AI initiatives into meaningful, revenue-generating products.
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We’ll now explore how bringing in former Avalara president Ross Tennenbaum as CFO could reshape Dropbox’s existing investment story.
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To own Dropbox today, you have to really believe that the company can transition from a mature cloud storage company with declining revenues and paying users to a more valuable, AI-enhanced productivity platform, while keeping its strong cash generation intact. The CFO transition to Ross Tennenbaum appears to be in line with that shift, but doesn’t materially change the near-term reality that the key catalyst is successful monetization of Dash. The biggest risk is that new AI products will not be able to offset the headwinds in core storage.
Of the recent developments, the April 2025 upgrade to Dropbox Dash is the most relevant, as the CFO change comes as Dash becomes increasingly capable across Slack, Teams, Canva, and Jira. That upgrade underscored management’s intent to use AI search and workflow tools to increase ARPU and reduce churn, which is now squarely Tennenbaum’s job as investors weigh whether AI investments can counter revenue pressure and increasing competition from major platform suites.
Still, investors should be aware that if Dash and related AI tools don’t gain traction quickly enough,…
Read the full story on Dropbox (it’s free!)
The Dropbox Story expects revenue of $2.5 billion and profits of $494.6 million by 2028. This assumes a 1.1% annual revenue decline and profit increase of about $9.2 million, compared to $485.4 million today.
Find out how Dropbox’s predictions yield a fair value of $28.12, in line with the current price.
Three estimates of the fair value of the Simply Wall St Community range from $28.13 to over $25,700, showing how far individual opinions can differ. Against that backdrop, the central question of whether AI products like Dash can offset declining core storage revenue becomes a useful lens through which to compare these different expectations and see what really matters for Dropbox’s future performance.
