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Dropbox's Drew Houston is betting everything on a new future for work

Dropbox's CEO explains how the pandemic changed the way he thinks about both Dropbox the company and Dropbox the product.

Dropbox CEO Drew Houston

Drew Houston said that when the pandemic hit, he and his team realized the future of work was changing — and Dropbox needed to keep up.

Photo: Dropbox

The first thing Dropbox CEO Drew Houston did when the pandemic hit was roughly what most other CEOs did: worry like crazy, send his employees home, and just try to find a way to keep going. But pretty quickly, Houston and his team started to realize that 2020 was going to bring lasting change to the way people work. Change that would stick around, in some form, long after the pandemic ended. And they felt like Dropbox needed to lead the charge in figuring that out.

"In a lot of ways," Houston said over Zoom, where he said he now spends nearly all his waking hours, "you can sort of squint and be like, 'I can imagine how this could really open up a new world.'" He compared it to the early days of the internet: Everything's basic and primitive, nothing quite works right, but if you can see through the growing pains, you'll see there's something big on the other end. "It's the same thing with distributed work," Houston went on. "This promise has been around since the '80s, with telework and things like more flexibility, being able to work from anywhere, not being stuck in commutes all day. Maybe we're actually on the cusp of delivering on that promise."

Much of this seems obvious now: that the future of work won't look like it has before. But what, exactly, does the new world look like? What are its rules, its routines, its practices? What new tools, new skills, new societal shifts does it require? Those are the questions most CEOs are still asking. Houston and Dropbox are a bit further ahead: They've spent the last eight months overhauling both Dropbox the product and Dropbox the company in an effort to help define the future of work. Houston called 2020 "a really bad, buggy beta test of distributed work." Now he hopes he's on the leading edge of designing a system that works.

Not long after sending everybody home, Dropbox started researching itself. Employees were sent surveys with questions about remote work and office life. Teams started testing new ways of work, like a four-day workweek or a much more flexible schedule than a 9-5. The company also commissioned the Economist Intelligence Unit to dig into the pros and cons of a distributed workplace. All that research turned up a huge variety of opinions, but a few kept coming up: There are lots of problems with remote work, particularly for people with kids, and most people missed having face-to-face interactions of some kind. But nobody liked commuting, nobody liked being tied to one city, and everybody was into the idea of having a more flexible schedule.

In October, Dropbox announced it was rethinking its whole workplace structure. Instead of requiring everyone to go to the office, it was becoming a "Virtual First" company. That comes with three big changes.

First: Dropbox's offices are turning into "Dropbox Studios," places people can go to meet or collaborate or just hang out with their colleagues (but most work will get done at home). This is a big change for Dropbox, which has had some of Silicon Valley's coolest offices — complete with in-house karaoke bar, garden roof and screening room — and has long believed that workplaces should be somewhere people feel at home. There will be fewer individual desks and closed offices, and more conference rooms and group-hang spots. (And probably still an in-house karaoke bar.)

Dropbox offices Dropbox has always had cooler offices than most, but now they'll be known as "Studios" and used only for collaborative work.Photo: Dropbox

Second: The 9-5 workday is going away. Instead, Dropbox employees will be able to work flexible hours, with a window of time in the middle of the day when everyone is expected to be available. That's when managers can schedule meetings, for instance, but it also provides what Houston hopes is the right amount of structure. "People are going to have different preferences, different needs," he said. "But they need some like guidance and coordination. You need some lines to be coloring in, even if you want to let people do the coloring."

Third: Dropbox, like practically every other company on the planet, is rethinking the tools it uses for most parts of the business, from communications to HR to productivity. It's trying to do it in an open way, too, building a Virtual First Toolkit for everyone to see and adapt.

Here's where Dropbox the company overlaps in a big way with Dropbox the product; Houston seems to sense that this is a moment for Dropbox to become the center of a new kind of workflow and workplace, and doesn't want to miss it.

The other thing Houston and his team did in March was sit down and completely rethink their product roadmap. The company's been a boon to remote workers for years, making it easier to sync and share files, but Houston is always in search of new problems to solve, and there were suddenly a lot of them. "Even just something like, 'How's everyone doing today, and what are we working on?' That's a question that's very easy to answer when you're physically together and very difficult to answer when you're not." How to keep work moving forward, how to make small talk with co-workers — all of the things people take for granted when the answer is "lean over the cubicle wall" — suddenly felt complicated.

As Dropbox has invested further into tools like a password manager, a digital signature app and the Paper note-taking app, it's starting to look more like a true competitor to Office and Google Workspace. Houston said that's not the goal, because who needs another one of those? Houston's not interested in competing with Zoom or Slack, or becoming yet another super-powered project-management tool.

Dropbox HelloSign Dropbox is much more than a hard drive in the cloud now, with features like password managers and digital-signature tools.Photo: Dropbox

But he also doesn't want to just keep being a hard drive in the cloud. He's been trying to get past that for a while, actually. "One element of the Dropbox experience people love is that it just works," he said. Users can set it, forget it and move on with their lives. But "there's only so much kind of painting on that canvas," Houston said — only so much he can do inside a Mac user's Finder app. So the company's spent the last couple of years working on a much richer desktop app, in which users can comment, organize, take notes on and generally do work with their files in a much broader way. The question for Dropbox, then, was how far to take the idea going forward. Where did it want to get involved, and where did it want to let other apps do their thing?

The result of all that thinking is the new version of Dropbox Spaces, which is out in private beta starting on Tuesday and coming to all Dropbox users early next year. The idea is to give people a place to put all their stuff — files, notes, comments, tasks, everything — in a way that's easy to organize, share and manage. In a way, it's not much of a departure from what Dropbox has always been about: making all your online stuff easy to find and access. It's just that the definitions of "online stuff" and "access" have broadened so much since the days of PDFs and MP3s.

To explain, Houston uses the example of this very product launch. "There's a lot of stuff associated with it," he said. "A lot of Slack messages and docs, PowerPoints, Paper documents, Google Sheets, whatever. I've got 10 different places to see what's going on. I can't just click, like, 'Launch Project.'" Going forward, he said, Launch Project might be a Space, with all that stuff in one place. Want to edit in Figma? Go for it. Figma's great. But the latest version of that file will still be in Dropbox, where everyone can see it.

The first version of Spaces launched in September 2019, with some of those same themes baked into the product. Some users didn't like the new direction, though, complaining that their simple file-syncing tool had turned into a heavy desktop app that didn't seem to add many new features. The new version is meant to feel much faster, more polished, and crucially more worthy of its own window. "It's much more true to that vision that we laid out," said Seiyonne Suriyakumar, a product marketing lead at Dropbox.

Dropbox Spaces 2.0 Dropbox Spaces is meant to be a single place for everything involved in a project, no matter where it comes from.Photo: Dropbox

The idea of bringing all a user's files into one place isn't exactly novel. Anyone dealing with dozens of logins, inboxes and notifications could describe the problem for themselves. But Houston is convinced that nobody's solved it yet and that Dropbox might have the best chance to do so. "There's all these intergalactic battles" between companies like Google and Microsoft fighting for workplace supremacy, he said, "and they put walls up to actually create that friction. In some ways, it's an intentional decision for competitive reasons. And the end user's kind of caught in the crossfire."

It's also just really hard to figure out how to support all those different files and formats in such a way that they can be previewed, shared, saved and organized in the same place. "How do you make this universal translator that speaks all the different platforms, supports all of them, and makes it just work, and builds a kind of full collaborative envelope around everything you're doing? That's not easy to do." It's even taken Dropbox a few years to get the technical infrastructure right, to support all the stacks of all the different companies.

The most ambitious way Dropbox is changing, however, has to do with communication. It's not trying to build a Slack competitor — though, if you squint a bit, you could see how it might get there — but it's definitely trying to bring more human interaction into its file system. "In some ways," Houston said, "we're taking the shared folder and just taking the mute button off." He said he's spent years watching people write emails with Dropbox links, or giving what he calls "driving directions to a file." Whole Slack channels exist just to alert people to Dropbox channels. "Why do we have to do this," Houston wondered, "when I'd rather just click on the thing and be like, 'I'm done, can you look at it?'" Ultimately, that seems to be the primary reason behind Spaces, and the thing Dropbox just could never do inside the Finder app.

He also said he's not sure exactly how all this remote-work stuff will pan out. "We're still in the chaos phase," he said. Until lockdowns end, all theories about hybrid workplaces will remain theories. But Houston said there's upside in trying to be ahead of the curve, even if some of his guesses — both in the product and in the company — turn out to be wrong. "So much more of the planet is going to be working in a distributed way," he said. "And if you want to design for the future of distributed work, you better live that way yourself. It's a lot easier."

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