Drew Houston, founder of Dropbox, announced on May 26 that he will step down as CEO after 19 years and transition to executive chairman [1, 2]. Houston and Ashraf Alkarmi, Dropbox’s product chief, will share leadership as co-CEOs during the transition, with Alkarmi set to become sole CEO in due course [1, 2].
Houston founded Dropbox nearly 20 years ago at age 24, growing it into a company now serving over 18 million paying users [1]. He said, "I think my 18-year-old self would be high-fiving me... Dropbox is something that a percentage of the planet still uses" [1].
Dropbox’s market capitalization stands at just over $6 billion, down from its IPO peak and a $10 billion valuation in 2014 [1]. The company surpassed $1 billion in annual revenue in 2017 and $2 billion about four years later, though recent revenue levels have been flat or slightly declining [1]. Dropbox faces stiff competition from rivals including Google, Apple, Amazon, Microsoft, and Box [1].
Alkarmi joined the company in November 2024, shortly before Dropbox cut about 20% of its workforce amid softening demand [2]. Houston praised Alkarmi as a leader, saying, "Early in running Dropbox, someone gave me a piece of advice: before you hire anyone, ask yourself if you'd feel good about your little brother or sister working for this person... Ashraf is that leader." He added, "Ashraf cares deeply about the people doing the work, and tells the truth even when it's hard and disagrees with me when I'm wrong." [2]
Alkarmi has overseen the launch of new AI products at Dropbox and emphasized the need to "keep innovating aggressively" during the AI era [2]. The cloud storage company will be led jointly by Houston and Alkarmi through the transition, with Alkarmi eventually taking full control as CEO [1, 2].
