Drew Houston is stepping down as Dropbox CEO after 19 years, with Ashraf Alkarmi — former Vimeo CPO and Amazon product leader — named co-CEO effective immediately. Houston plans to pursue an AI-focused entrepreneurial venture. Dropbox's market cap has halved since its 2018 IPO as Google Drive, Apple iCloud, and Microsoft OneDrive commoditized cloud storage. The company's core business grew less than 1% year-over-year in Q1 2026, despite efforts to reposition around AI with products like Dropbox Dash. Alkarmi's mandate is to find a product-led growth path for a company that has already cut 16% of its workforce and faces well-resourced platform competitors building the same AI capabilities.
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