• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Exclusive

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

An hour in the Oval Office with President Trump.

Successreturn to office

Dropbox’s CEO has a message for bosses who want workers to return to office: ‘They’re not resources to control’

By
Jane Thier
Jane Thier
Down Arrow Button Icon
By
Jane Thier
Jane Thier
Down Arrow Button Icon
October 15, 2023, 9:00 AM ET
Drew Houston, CEO of Dropbox, says you have to let go of control when managing a remote workforce. “But if you trust people and treat them like adults, they’ll behave like adults. Trust over surveillance.”
Drew Houston, CEO of Dropbox, says you have to let go of control when managing a remote workforce. “But if you trust people and treat them like adults, they’ll behave like adults. Trust over surveillance.”Kelsey McClellan for Fortune

What would Drew Houston, CEO of Silicon Valley software giant Dropbox, say to fellow CEOs—like Google’s Sundar Pichai or Meta’s Mark Zuckerberg—who seem to believe that three days a week in person is crucial for company culture? 

Recommended Video

“I’d say, ‘Your employees have options,’” Houston told Fortune this past week. “They’re not resources to control.” 

While Dropbox used to work almost entirely at its Bay Area headquarters, Houston has completely warmed to a distributed model since the pandemic and is mystified as to why other leaders haven’t joined him. (Houston founded Dropbox in 2007, the year after he graduated from MIT, and has been its CEO ever since.) 

“From a product design perspective, customers are our employees. We’ve stitched together this working model based on primary research,” he told Fortune at Dropbox’s WIP Conference—its first in-person event since 2019—in New York on Tuesday. “We’ve just been handed the keys that unlock this whole future of work, which is actually here.” 

In April 2021, right when most of the country became eligible for vaccines and people began reconvening around the globe, Dropbox encouraged the opposite. It officially announced its intent to go Virtual First, which meant employees were free to work remotely 90% of the time, commuting in only for the occasional meeting or happy hour. 

It was a big commitment, seeing as Dropbox had just shelled out for what Houston said is one of the most expensive commercial office spaces in the Bay. But it pivoted quickly, downsizing its real estate footprint from 735,000 square feet to 600,000 and rerouting those fancy office perks right back to workers. Dropbox employees are given a quarterly allowance to use on “what really matters to them,” a Dropbox spokesperson told Fortune.

Granted, not everyone got to appreciate the perks. In April, Dropbox laid off 500 employees—16% of its staff—due to “slowing growth” and “the AI era” requiring a reallocation of resources. 

As tech company after tech company has reneged on its commitments to work from anywhere, Dropbox hasn’t budged. “The unlock for us was realizing we’re not going back to the office as we know it, but we also don’t want to be stuck at home on Zoom for the rest of our lives,” he said. On the other hand, “What’s the ideal environment? A windowless conference room?”

The 90/10 rule

Today, Dropbox doesn’t mandate any amount of in-office presence, though the company maintained the 90% remote “pencil sketch” outlined in 2021, Houston said. “Where we ended up was, there’s no substitute for the in-person connection, but let’s do it in a great way, [and] let’s let people do most stuff remotely.” 

Houston and his team have found, in practice, a handful of two- or three-day offsites per quarter—10% of the year—works best for their people. Crucially, it provides that oft-referenced cultural connect and brainstorming time that pro-office zealots insist upon, without exhausting workers with a commute grind or needless hours in drab conference rooms. The key, Houston said, is that when they’re in person, employees know they’re personally deciding to opt in, rather than being yanked. 

The company also encourages flexible work hours. All meetings must narrow in on the “three D’s” of discussion, debate, or decision-making, and they can be held only between noon and 4 p.m. EST. “Any future-of-work strategy we chose, we wanted to ensure that employees had control over not only how they work, but where they work,” Dropbox’s chief people officer, Melanie Rosenwasser, told Fortune last year. “We’re trying to put practices into place that, if adopted on a wider scale, make everyone more productive and efficient.” 

As any flexibility expert can tell you, flexible work does more than just satisfy workers. It also sends recruitment stats through the roof. Remote hiring has been “a huge superpower and unlock for us,” Houston remarked. “We’ve gotten so many executive vice presidents that don’t live in the Bay Area who are meeting their coworkers for the first time. Now we have L.A., Chicago, Boston—between dozens and hundreds of people are in these areas where we never had anyone.”

Houston also waves away the suggestion that managing a worker in Boston is any different for him than managing someone under his thumb in San Francisco. “You need a different social contract, and to let go of control,” he acknowledged. “But if you trust people and treat them like adults, they’ll behave like adults. Trust over surveillance.” 

While many of Houston’s contemporaries are grumbling over employees’ intransigence—or worse, tracking their badge swipes—the Dropbox chief has been heartened by the challenge of evolving his company. “Turning Dropbox into this lab for the future of distributed work has been awesome,” he said. “It’s a working model we’ve been able to build a few years in the future, and stub our toes on problems and then design this whole portfolio.”

At the Fortune Workplace Innovation Summit, Fortune 500 leaders will convene to explore the defining questions shaping the workforce of the future—delivering bold ideas, powerful connections, and actionable insights for building resilient organizations for the decade ahead. Join Fortune May 19–20 in Atlanta. Register now.
About the Author
By Jane Thier
LinkedIn iconTwitter icon
See full bioRight Arrow Button Icon

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Success

Solo founders are using AI to do the work of entire teams—but going it alone has limits
AIEntrepreneurs
Solo founders are using AI to do the work of entire teams—but going it alone has limits
By Beatrice NolanMay 18, 2026
5 hours ago
shyam
CommentaryHealth
World Economic Forum: women’s health gets only 20% of R&D funding. We must seize this $1 trillion opportunity
By Shyam BishenMay 18, 2026
9 hours ago
Stressed job seeker
SuccessGen Z
Gen Z is right about the job hunt—it really is worse than it was for millennials, with nearly 60% of fresh-faced grads frozen out of the workforce
By Emma BurleighMay 17, 2026
1 day ago
‘No one was coming to save me’: How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn’t fix
Successreese witherspoon
‘No one was coming to save me’: How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn’t fix
By Sydney LakeMay 17, 2026
1 day ago
Despite degrees being slammed as ‘useless’ by Gen Z, data shows graduates have had the lowest unemployment rate of anyone for the last 20 years
Successunemployment
Despite degrees being slammed as ‘useless’ by Gen Z, data shows graduates have had the lowest unemployment rate of anyone for the last 20 years
By Orianna Rosa RoyleMay 17, 2026
1 day ago
tarot
AICulture
We talked to 12 tarot card readers who are using AI. They split in 2 camps, with big implications for the technology
By Ziv Epstein, Farnaz Jahanbakhsh, Vana Goblot and The ConversationMay 16, 2026
2 days ago

Most Popular

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
2 days ago
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
Economy
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
By Jason MaMay 17, 2026
20 hours ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
6 days ago
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
Success
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
By Sydney LakeMay 17, 2026
1 day ago
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
Innovation
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
By Jason MaMay 16, 2026
2 days ago
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
Politics
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.