Dropbox CEO Drew Houston to step down after 19 years at cloud pioneer

Drew Houston founded Dropbox nearly two decades ago at age 24, eventually becoming a household name in Silicon Valley and the first tech entrepreneur to take a company from the Y Combinator incubator program all the way to the public market.

Now, at 43, Houston is ready to do something else. He’s informing staffers on Tuesday that he’ll be transitioning into an executive chairman role after an initial period sharing the co-CEO title with Ashraf Alkarmi, who is being promoted from product chief. Alkarmi will eventually take over the top job on his own.

By almost any measure, Houston has had a great run at Dropbox, helping pioneer the cloud storage market, competing head-to-head with Google and Apple and building a net worth of more than $2 billion, thanks to substantial ownership in his company. But in the land of outsized expectations, Houston has overseen a company that peaked too soon and never became a generation-defining brand.

Dropbox’s current market cap of just over $6 billion is down by half from the high price on its first day of trading in 2018, and is below the $10 billion valuation it was ascribed by private market investors in 2014. Meanwhile, Airbnb, another early breakout hit from Y Combinator, has a market cap of close to $80 billion, and CEO Brian Chesky is credited with upending the hospitality industry.

Houston, who created Dropbox due to a “personal frustration” with constantly losing USB sticks when he was in college at the Massachusetts Institute of Technology, brushed off the Airbnb comparison.

“I think my 18-year-old self would be high-fiving me,” Houston told CNBC in an exclusive interview, noting that Dropbox is “something that a percentage of the planet still uses.”

In its latest quarterly earnings report, Dropbox said it has more than 18 million paying users, and the service remains popular with media professionals, graphic designers, architects, and others who share files and photos as part of their daily work.

Dropbox topped $1 billion in annual revenue in 2017 and surpassed $2 billion four years later. But revenue is roughly flat over the past two years and declined slightly in 2025.

The company’s perpetual challenge has been to distinguish itself from the swarm of competition, which includes Apple and Google as well as Amazon and Microsoft. Then there’s longtime rival Box, which is still run by founder Aaron Levie and faces similar obstacles. Box is valued at just over $3.5 billion.

The latest hurdle for Dropbox, and the whole category of subscription software, is…