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It might get weird: why Dropbox employees are goofing around on company time

The cloud storage giant looks to the past to hack its future

Out in the San Francisco bay, behind AT&T Park, a giant version of Dropbox’s “open box” logo bobs up and down in the waves. It’s actually a paddle boat, with the giant box built on top; inside, two of Dropbox’s employees are pedaling it around with no idea where they’re headed.

Meanwhile, the company’s nearby offices are humming with a bizarre but infectious energy. In one corner, a scooter retrofitted with two motorized wheels, a webcam, and a MacBook Air navigates between conference rooms without any human guidance. A drone flies erratically overhead, snapping pictures with its camera and automatically uploading them to Dropbox. Another corner of the office features a custom T-shirt-printing station modeled after a sandwich shop — complete with a “take a number” dispenser, a deli case full of the day’s “ingredients,” and Dropbox-themed deli paper to wrap up the finished goods. CEO Drew Houston hunkered down in a corner, coding with three monitors surrounding him, headphones on, Winamp running.

Welcome to Hack Week.

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"This week is a great reminder that [Dropbox] started as basically a large hack week project, and that we need to continue being bold and ambitious," says Max Belanger, a Dropbox engineer who’s also one of Hack Week’s organizers. And for a company with more than 800 employees, there’s a huge diversity of work on display — of the 130 projects completed during Hack Week, a huge portion of the creations have next to nothing to do with the company’s products directly. "We don’t actually set any restrictions," Belanger says as we tour Dropbox’s end-of-the-week expo, where everyone shows off their projects and votes on their favorites. "A lot of people are actually going to work on projects that are completely unrelated to Dropbox itself."

Dropbox wants to keep its image as a Silicon Valley playground

That’s entirely by design — hack weeks and hackathons have become increasingly common ways for companies to let their people off the chain to see what happens, regardless of whether it’ll bring in revenue or reveal new innovations to push the company forward. "Part of the spirit of Hack Week is getting out of your comfort zone, learning something new, doing something unusual," says engineer Alicia Chen. While drone and T-shirt projects may have little financial value, they certainly help Dropbox sell itself as a great employer. And as the company more than doubled its headcount over the last year, there’s no doubt that it wants to keep its image as a Silicon Valley playground where anything can happen — something it has in common with most of its contemporaries, from the smallest startups all the way up to Facebook.

However, a lot of other employees treat Hack Week as a chance to focus on specific problems. Last year Chen worked on the oft-requested "two account" feature, which lets business and personal accounts live side-by-side. Dropbox had been struggling with this for years, but Chen lead a team that cracked it wide open at the 2013 Hack Week. "There was a team of about five of us who built the desktop client for multi-account — we were actually able to demo an almost fully functioning Mac and Windows version by the end of the week," she says. "Before that, it had been very theoretical."

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While there aren’t formal follow-ups to Hack Week creations, the right project can become a reality. "Show off that it’s possible," says Belanger, "and it’s not hard to convince people that it needs to happen." Dropbox launched the two-account feature after less than a year, and other Hack Week projects have been turned around significantly faster. "I was really impressed by the two-factor authentication project," remembers Chen. "It started with a couple of engineers and then everyone really geared up after hack week. I think we managed to ship it five weeks after hack week."

"Part of the spirit of Hack Week is getting out of your comfort zone, learning something new, doing something unusual."

Dropbox is quick to note that no projects being shown off at Hack Week are officially on any sort of product roadmap — they could never be heard of again. That said, there were a number of innovations developed over the week that could easily make their way into future products; they also do a good job of showing what engineers think is worth focusing on.

This year, Chen and her team put together a feature they called Drops. "The idea is it will be a submissions collector for, say, a teacher who wants to collect homework from a lot of students, or someone who wants to collect wedding photos from guests," she says, "which is where I first came up with this." Drops went on to win the "#ShipIt award" (given to the product closest to being ready to ship to users) at the Hack Week’s closing ceremony. Another project up for the award focused on extending the Carousel photo backup app to the TV. Chromecast was the platform of choice — over the week, the team added support for casting photos and videos from both the iOS and Android apps.

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Dropbox engineers also spent a lot of time working on tools for improved collaboration in shared Office documents (for those not using one of Microsoft’s online tools like Office.com), a problem as old as Dropbox itself. The company began tackling it earlier this year with Project Harmony, a feature that would let Office users see when others were accessing shared documents through Dropbox. There were at least three Hack Week projects building on those tools, trying to bring more Google Docs-style collaboration and editing to Dropbox — a pretty clear example of the company’s need to move beyond just managing simple files.

There’s also a lot of work that falls outside the silly and the product-focused — with 800 people, there are plenty of employees who don’t call themselves coders. One of the biggest such initiatives is Dropbox For Good, an ongoing charity program that donated Dropbox business accounts to non-profits and collected clothing for charities. Other projects focused on doing little things to make the lives of employees better, like new office maps with a grid system to help people find conference rooms easier or a giant panda two employees spent the week sewing. Of course, they also hooked the panda up to the Dropbox’s code logs and gave it glowing LED lights — if an employee breaks the code, the eyes light up red and a small screen chastises the employee at fault.

Getting back to its roots is a joke that Dropbox takes very seriously

Hack Week is about getting the company "back to its roots." The catchphrase is thrown around enough that it’s a bit of a joke at this point, but it is something taken seriously from the top of the organization down through everyone I met. "Things have gotten a little more formal — back in the day, people were here till 2AM, the Tuck Shop [Dropbox’s kitchen] was flipping burgers the whole time," says Jon Ying, one of Dropbox’s first employees and a prime organizer of Hack Week. "But last night I was here late and there weren’t many people left — there’s a lot more people with kids and families than there used to be."

With its Hack Week, Dropbox is trying to reclaim the feeling of a small team coming together and pushing themselves to create something new. Like numerous other companies in and outside of Silicon Valley with similar programs, Dropbox is now big enough that it can no longer be a free-for-all of engineers coding whatever they please — but there’s a benefit to infusing the office with that spirit, even if it’s only for five days. Dropbox made that clear at the awards ceremony, when engineer and MC Jean-Denis Greze noted that awards were almost meaningless in the context of Hack Week — what’s most important is the collaboration. Anything Dropbox can put into a product and ship is a bonus.

Photography by Kara Brodgesell for Dropbox

Dropbox Hack week, in photos

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Scooter's Sandwich Shop was a fixture during Hack Week, printing t-shirts on demand.