Dropbox's CEO is Stepping Down after 19 Years

Dropbox Co-Founder Drew Houston is stepping down from the company’s CEO position after 19 years.

This week, he told staffers that he will be transitioning to an executive chairman role following an initial period sharing the co-CEO title with Ashraf Alkarmi, who is being promoted from product chief to the CEO position. 

Drew has been instrumental in positioning Dropbox as a pioneer in the cloud storage market and has helped the company compete with large industry rivals like Google and Apple. 

Under Drew’s leadership, the company has become an industry leader in cloud storage that has brought in more than US$1bn in yearly revenue, every year since 2018.

Drew helped create the brand due to what he describes as a “personal frustration” with misplacing USB sticks during his education at the Massachusetts Institute of Technology.

Speaking in an interview with CNBC, Drew says “I think my 18-year-old self would be high-fiving me," adding that Dropbox is “something that a percentage of the planet still uses”.

Concerns in the SaaS industry

In its latest 2026 Q1 earnings report, Dropbox says it currently has more than 18 million paying users and the service remains popular with media professionals, graphic designers, architects, and consumers who share files and photos as part of their daily work.

While revenue has stayed above US$1bn since 2018, it has flattened for the past two years and declined somewhat in 2025.

Dropbox still faces challenges amid competition from companies like Amazon and Box, in addition to pressures to implement technologies like AI, which has dominated the industry for the past three years. 

The software sector has experienced widespread anxiety over concerns that foundation models from OpenAI and Anthropic could enable simpler tools that displace software existing products.

Despite these concerns, Dropbox shares have held up better than others, with companies like Monday.com, HubSpot and Asana losing more than 60% of their value, compared to Dropbox’s considerably smaller 5% stock reduction in 2025.

“Whenever there’s a new technology, people extrapolate very quickly,” Drew says. He adds that companies make assumptions that may be “directionally correct” but take years or even decades longer to play out.

Discussing the concept of the “SaaS Apocalypse”, Drew says “[I’ve] never met a Dropbox customer who’s like, ‘I’m just using so much ChatGPT I’m going to cancel my Dropbox subscription.’”

Attracting investors with AI integration

Analysts at Monness, Crespi, Hardt & Co. said in a report earlier this month after earnings that Dropbox is making progress with AI integration, highlighting its AI-powered Dash feature that customers can use to more easily search and interact with documents and messages across third-party apps. 

The analysts added that said the AI tool and the company’s valuation are two reasons that value investors may be drawn to Dropbox.

Drew now plans on building something AI, not just at Dropbox.

“It’s all cliché, right?” AI is reshaping every aspect of how we live, and I’m sure that I’ll have no shortage of ideas and stuff to work on,” he says.

He adds that he wants to do something entrepreneurial in AI as “there’s never been a more exciting period to be building things”.

Regarding his decision to leave, Drew says there was no one reason for his departure, saying: “Part of me has always thought, oh yeah, I’ll be the CEO of Dropbox until my last gasp of my career. There’s never a perfect time, there was no part of me where I was like, ‘oh, this date is the date where it’s going to happen.’”

“I trust the right leader,” he adds. “The company’s in the right place.”