Inside Dropbox’s Reverse-Engineered Company Culture
Five years ago, Dropbox famously reverse engineered Apple’s Finder system to introduce its own icon onto the top dock, with its folders fully integrated and a little green checkmark when files are synced. The hack was so nifty that it attracted acquisition interest from Steve Jobs.
That original approach — thinking a system through and intuiting what it can do — turns out to be central to Dropbox, continuing through to the company’s recent product launches, like automatic camera uploads and integrations with various phone manufacturers.
A few months ago, when my Dropbox client popped up to ask me if I wanted to automatically upload my photos each time I plugged in my iPhone, I wondered how the heck it had intercepted my operating system. But after a few times seeing the alert, I gave it a try, and now I’ve come to rely on my photos and videos arriving on my desktop.
“No one was asking us for camera uploads,” Dropbox CEO Houston told me in an interview during Dropbox’s recent companywide Hack Week.
But Dropbox anticipated that need and figured out a convenient way to address it.
The spirit of reverse engineering seems to permeate the way Houston and his co-founder Arash Ferdowsi run their company — both the Dropbox product and the Dropbox team.
“When we first came out, people thought this problem [of storing files online] was solved,” Houston explained. “So we could be creative because we had no constraints.”
Houston is trying to keep that mentality intact as his company grows.
When I asked Dropbox employees at the Hack Week what the company’s culture is, most answered that it is about freedom.
At Dropbox, they said, job titles and formal organization are less important than getting stuff done, because everyone is smart, and there’s just so much left to be done to help the world store and sync their files across every device.
“We’re walking through a grove of low-hanging fruit that is slapping us in the face,” said Jon Ying, one of Dropbox’s first employees, who has become sort of the keeper of the company spirit, and recently led a project to write up Dropbox’s values.
Dropbox may be young, but its list of company traditions is long. It definitely includes karaoke — Houston and Ferdowsi and the gang are reportedly regulars at The Mint in San Francisco (The Mint, let it be said, is an intimidatingly serious karaoke bar.)
The company ends meetings with a simple, hokey cheer, “One! Two! Three! DROPBOX!”
Unlike some other promising start-ups, Dropbox seems to have lost only a few employees over the years — it declined to say exactly how many.
The first Dropbox employee, Aston Motes, recently left to found his own stealth start-up. When I contacted him to ask about Dropbox and why he left, Motes eagerly reminisced about Dropbox’s fall kickball-league victory, its karaoke nights and Whiskey Fridays. He also went on at length about how Dropbox engineers think about delighting users, rather than just executing implementations. It was clear the Kool-Aid hasn’t worn off yet!
And while Dropbox might have hired at a relatively slow rate in its early years — the company hovered around 10 employees for what was probably way too long, Ying said — this year, it jumped up rapidly, to about 170 people.
Considering Dropbox is tackling the unsexy topic of cloud storage, convincing people to take a job at Dropbox seems to be a relatively easy sell.
With millions of users, lots of potential upside (that is, if new Internet stocks ever turn around), venture money in the bank, revenue streaming in and healthy respect in the market, Dropbox appeals to new hires by giving them lots of opportunity to make an impact, both on the product and, potentially, the world at large.
For instance, one Dropbox engineer I met, Thomas “Tido” Carriero, graduated from Harvard with a computer science degree in 2008 and took the cross-country pipeline straight to Facebook. After working on Facebook’s ads, he was most recently an engineering manager on Timeline for Pages.
Since joining Dropbox four months ago, Carriero has helped start a growth team from scratch. He told me that at Facebook, introducing a product like ad auctions might have improved performance by 5 percent. Then, a year or two later, tweaks might bump it up another tenth of a percent.
But at Dropbox, an intern recently changed the subject line of a user-email blast, and saw a 15 percent gain in effectiveness within a week, Carriero said. That’s real impact.
Carriero’s personal goal for his Hack Week projects — which involved changing the Dropbox landing page to invite people who aren’t registered to sign up rather than log in — was to add at least one million Dropbox signups in the next year.
When I talked to him during Hack Week, Carriero had already been able to push his newly created concept out to 1 percent of visitors, and could see that it was generating thousands of new registrations.
That kind of freedom isn’t unusual. Jon Ying — the guy with the great “low-hanging fruit” metaphor — told me he joined Dropbox as a part-time community manager four-and-a-half years ago, because he knew co-founder Arash Ferdowsi from growing up in Kansas City.
One day, Ferdowsi told him he didn’t want Dropbox’s “404 error” page to be so boring. “I remember you like to draw,” he told Ying, who had majored in economics at UCSD. So Ferdowsi bought some colored pencils at the Walgreens downstairs, and Ying drew up “Psychobox,” an M.C. Escher-esque take on the Dropbox logo that has since become a sort of mascot.
Ferdowsi’s next leap was, “If you know how to draw, you can do Web design.” So he grabbed a pirated copy of Photoshop, and Ying started doing early Dropbox design work.
It’s this mentality — “you’re smart, figure it out” — that Ying described as key to Dropbox. Ferdowsi and Houston’s special talent is perceptively identifying what people are good at and letting them do it, Ying said.
In a sense, just like Ferdowsi and Houston reverse engineered the Apple Finder to do things beyond what was thought capable, Dropbox tries to push their employees to their full potential. “It’s an obsession here to make sure people are happy and learning and challenged,” Carriero told me.
Asked to compare Dropbox’s culture to that of other companies, Houston was ready with a set of incisive descriptions. “Google is super analytical,” he said. “Apple is about design. Facebook is about go fast and dominate.”
Meanwhile, Dropbox combines a bit of each of those traits, Houston said, around its goal of figuring out how to be useful, and bringing its tools to everywhere people need them.