Dropbox CEO Drew Houston on his plans to step down from his role after nearly two decades: 'I think my 18-year-old self would be…

Dropbox co-founder and CEO Drew Houston is stepping down from his leadership role after nearly two decades at the company. He will transition to executive chairman while continuing to share co-CEO responsibilities with current product chief Ashraf Alkarmi before the latter fully takes over. Houston said there was no specific event behind the decision and reflected on his journey since founding Dropbox at age 24.



Speaking about Dropbox’s trajectory and his personal career, Houston told CNBC, “I think my 18-year-old self would be high-fiving me,” noting that Dropbox is “something that a percentage of the planet still uses.”



Houston founded Dropbox after what he described as a “personal frustration” with losing USB drives while studying at the Massachusetts Institute of Technology. The company later became one of the first startups from the Y Combinator accelerator to go public.




Drew Houston on why there was ‘never a perfect time’ to step down




Houston said his decision to move away from the CEO role was not tied to a fixed timeline. He said, “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.’”



Ashraf Alkarmi, who joined Dropbox from Vimeo in late 2024, will eventually become the sole CEO. Houston said the company has become “a lot more responsive to our customers and is taking bigger swings on innovation” since Alkarmi’s arrival.



“I trust the right leader. The company’s in the right place,” Houston added.



Dropbox currently has more than 18 million paying users, according to its latest earnings report. The company crossed $1 billion in annual revenue in 2017 and surpassed $2 billion four years later, though revenue growth has flattened over recent years. Houston said he intends to work on entrepreneurial projects in artificial intelligence (AI) after stepping back from day-to-day leadership at Dropbox.



“I’m not going to be racing sailboats,” said Houston, who also serves on the board of Meta. He added that he wants to build something in AI because “there’s never been a more exciting period to be building things.”



“It’s all cliche, 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,” Houston highlighted.



Houston also addressed concerns about AI affecting software subscription businesses, noting that assumptions about technological shifts often take longer to materialise than expected.



Regarding fears around a broader impact on software companies, he said, “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.’”



Alongside the leadership transition, Dropbox announced that Mike Torres will join the company as chief product officer from Google in July.