Dropbox CEO: 3 insights from leading a ‘virtual first’ workforce

The current generation of smart tools isn’t all that smart. Want proof? Look at your phone’s inbox.

“Eighty thousand unread emails — for what question is that the right answer?” Dropbox co-founder and CEO Drew Houston asked during an Oct. 14 talk at MIT.

Eighty thousand unread emails might be more of a head-of-a-billion-dollar-company problem, but Houston’s point applies to many of today’s knowledge workers. The physical separation between work and home has largely been erased thanks to the shift to remote and hybrid office environments. Knowledge workers spend much of the day in front of a screen responding to phone notifications, appearing on video calls, or tracking down and managing collaborative work saved in a cloud space.

“Instead of the tools helping us do the work, the tools kind of became the work,” Houston, SB ’05, said during the talk with Dan Huttenlocher, dean of the MIT Stephen A. Schwarzman College of Computing.

Houston’s spent the better part of the past 18 months thinking about how to reverse that course and relieve knowledge worker burnout — largely because his cloud storage and collaboration software are some of the tools increasingly replied upon in the new hybrid work environment. But he's also looking to protect his own workers from feeling burned out and disconnected in a remote space.

“We need to both design better tools and a smarter system. It's not just the individual parts but how they're woven together,” Houston said. “I think the same way we had a new generation of cloud tools that revolutionized how we work — and have all these advantages that we couldn’t imagine not having now — I think we're going to have a new generation of smart tools.” 

During his visit to MIT, Houston spoke with Ideas Made to Matter about how Dropbox is rethinking those next generation tools, and shared some achievements, challenges, and observations that have come from leading a company in the pandemic era.

There’s no substitute for in-person experience

In October 2020 Dropbox announced a “virtual first” working model in which employees would spend most of their time at home but also schedule visits to a “Dropbox Studio” for in-person work with teammates. The permanent studio locations include San Francisco, Austin, and Dublin, Ireland.

“If you really curate that experience, make it great and focus more on how do we really bond and build relationships … our belief is that gases up your relationship tank and that carries you forward for the rest of the quarter, and then every quarter you repeat,” Houston said.

But days after the studios opened this summer, Dropbox employees around the world were sent home due to rising COVID-19 cases and the onset of the delta variant. The company is taking a regional approach to reopening studios and has reopened a few locations.

Despite the closures, Houston said he’s happy with the virtual first approach.

“There's so many great things about the remote environment,” Houston said. “You have a lot of flexibility, you don't have to commute. But there's no substitute for the in-person experience and technology can only go so far to simulate that. Going remote-only was not an option for us.”

At the same time, Houston didn’t want to order employees to be in the office for a set number of days each week, because workers would still be tethered to their desks in half-empty offices. The in-office requirement also wasn’t practical for employees who had moved out of state.

“That throws a wrench into all the models because then you're going to the office, but you've got that one person on your team who's really remote,” Houston said. “And they're not going to fly in for [a] meeting, so guess what, you're commuting to be back on Zoom, which is a new circle of hell in an open-plan office.”

‘Location agnostic’ jobs have expanded talent pools

While the pandemic has been a learning experience for his company, Houston said its impact has also been a “huge tailwind on recruiting.” Before the pandemic, jobs at companies like Dropbox were limited to people who lived close to big cities like San Francisco, New York City, or Boston. Now, great jobs are “location agnostic.”

Those jobs are also reshaping hiring packages, as more and more candidates require workplace flexibility from potential employers.

“People will leave companies where they don't have flexibility for companies that do,” Houston said. “A company that doesn't offer that flexibility will quickly look as archaic as a company that doesn’t have a website.”

For a successful operations plan: be adaptable and iterate

Like many CEOs, Houston is doing what he can to predict and adapt to the changing work environment, both for Dropbox’s employees and its customers.

In late September, Dropbox released a suite of new products for remote and hybrid work customers to help organize their cloud content.

“In a lot of ways we need to solve very similar problems again in the 2021 context,” Houston said. “Because what used to be 100 icons on your desktop are now 100 tabs in your browser.”

As for leading his workforce, Houston said he’s taken an iterative and adaptable approach to operational plans, and he also looks to other remote-oriented companies for ideas. (Companies like Adobe and Slack announced their own “digital-first” approaches with scheduled in-person time for collaboration and to build relationships.)

Houston advises other companies to do the same, but also noted they don’t have to reinvent the wheel when it comes to a work plan.

“Just grab something off-the-shelf and tune it for what you want,” Houston said. “But that said, I think the pandemic offers a bunch of interesting management lessons: In total uncertainty you really have to be adaptable, there's always a silver lining in any crisis, and there's a lot you can do by just thinking about things from first principles.”

Those first principles mean getting back to the basics of a company. Start with a bunch of people who work at the company and ask what their workdays really look like in practice.

“That’s how we realized this 2-3 day a week thing [was] not going to be great,” Houston said. “We were willing to put a lot of chips on that bet. We’re really happy we made that bet. This is our business; we help people work more flexibility.”

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