With Mailbox, Dropbox moves beyond its cloud-storage beginni
Source: Nick Statt

As Dropbox transforms from its online-storage origins to a growing, multi-purpose platform, the company's head of design is orchestrating its app-centric future.

Dropbox's Mailbox for desktop beta opens to the public on Tuesday. Nick Statt/CNET

When Dropbox's product design team begins rolling out the desktop version of its email application Mailbox on Tuesday, the software will come with an experiment packaged in playfulness.

Called a betacoin, the anthropomorphic token equipped with eyes and a cartoony smile will let you pass the desktop beta of Mailbox onto a friend. Every current user of the iPhone and Android Mailbox app gets one betacoin invite, but completing certain tasks -- like achieving the zen-like state of "inbox zero" -- nets you more. The idea is an evolution of the email service's original rollout roadmap, which involved a waiting list for iOS users to help Mailbox scale as more than 1.5 million people hopped in line in the spring to discover what all the fuss was about.


Yet in betacoins, the online storage company is also able to embed a feedback mechanism we won't even know is there. As each token is doled out to Mailbox desktop users, the behavior that earned it will inform, alongside concrete user feedback, the way the app is tweaked before its final release. Designing both a way to help the beta spread organically while somewhat gamifying how the software learns about us fits in with the company's culture. At Dropbox, every stroke of design has a greater function to serve, the end being an ever more attractive service that nudges its way closer to the center of your digital life, starting with your files.

"Design has always been a big part of Dropbox. What's changed is the surface area of what needs to be designed," says Gentry Underwood, the company's head of design and the co-founder of Orchestra, the 13-person team that Dropbox purchased for a reported $100 million in March 2013 to acquire Mailbox.

A year and a half later, Mailbox's core principles have become one of Dropbox's flagship strategies for solving problems: use a dedicated solution, in app form, to tackle an issue like email that every modern Web user finds at least occasionally painful, often more than occasionally. Do it well enough and that user just might become a dedicated Dropbox customer.
Finding the constellation

It is just as naive to call Dropbox a cloud storage company nowadays as it is to call Apple a phone maker or Google a search engine. Dropbox, which now has 300 million users and more than 500 employees, is seven years old and still growing so fast that it needed to lease a second building in San Francisco's South of Market district in February. Since its 2007 debut as a Y Combinator startup, Dropbox's core mission has shifted as well.

"Dropbox has come from the magic folder to home for life," says Mailbox product designer Tony DeVincenzi. "We have this responsibility now of being the container for your most important stuff. It makes a lot of sense that we would build very specific and very considerate experiences on top of your most important stuff." It also helps that Dropbox is used as the authentication point for all of those experiences, bolstering use of its core storage service in the process.

For Underwood, who leads the product design charge, it's about seeing ahead as much as it is about dazzling with aesthetics. "The core promise of Dropbox -- being a home for people's [and] companies' most precious information -- that promise has to evolve into this world where information lives in more formats than just files and folders," he says.

Similar to how Facebook spun out its messaging, photo sharing, and timeline viewing functions as separate apps, Dropbox is designing an app-centric family, or what Underwood calls a constellation of solutions for which Mailbox was the beginning. Last April, which employees refer to with historical gravitas as "4.09," Dropbox launched Carousel, a way to upload every photo you take with your smartphone automatically to your Dropbox and to view it on-the-go without needing to keep the files locally on your device. Dropbox had a photo-management problem and instead of trying to bolt on a solution within Dropbox itself, the company focused a solution to a sharp point and released it as a standalone smartphone app.

"It's really about decoupling this more generalized tool that is Dropbox historically into these dedicated experiences that are more specific," Underwood says of the strategy.

Steve Jobs famously called Dropbox a "feature," not a product, back in 2009 when Dropbox CEO Drew Houston rebuffed Jobs' offer to buy the fledgling cloud-storage company. Five years later, Dropbox is still on a mission to refute that notion through its success as a platform, flush with $1.1 billion in cash and on its way toward a forthcoming IPO at a $10 billion valuation.
"The core promise of Dropbox has to evolve into this world where information lives in more formats than just files and folders."
Gentry Underwood, Dropbox's head of design

The company, alongside its more enterprise-focused rival Box, has long since lost the war on cloud storage pricing as larger companies such as Google, Microsoft, Amazon, and even Apple have joined a race to the bottom to entice consumers to sign up for their competing services. To stay out front, Dropbox is trying to succeed instead on the merits of its design. To overcome the pressure from above and continue establishing its value, Dropbox needs to prove that it can be the center of our digital lives in a way that operating system-makers like Apple and Google cannot, even as those giants keep designing new features to directly cut into Dropbox's dominance.

That's where Mailbox and Carousel play integral roles. Both apps are multi-platform, soon-to-be device-agnostic approaches to email and photo storage -- two product types Apple and Google have throw innumerable fixes at in an attempt to get us to shy away from third-party offerings. Yet both pieces of software represent Dropbox's vision for the future -- a promise that it can out-design even Apple when it comes to the most effective tools for managing our increasingly complicated digital lives.
Honing the knife and removing the elephant

"Often I think really great design disappears. You don't think about it, you don't pay attention to it because it's so effective that your experience of it is that it just works," Underwood says of the core design principles that drive both Dropbox and Mailbox. Coincidentally, "it just works" is an early Dropbox motto, plastered on walls at the company's first headquarters with the words "just work" bolded in blue.

"It's that 'of course' kind of feeling that I think is in many of the great products that we've come to know and love over time," Underwood continues. "Be it the fact that the next Kleenex comes out right after the one before, or the shape of your phone and the way that it's one giant piece of glass that's incredible adaptive to whatever function that you're using it for."

It is that philosophy that informed both Mailbox's migration to desktop and the development of Carousel. It's also why Underwood, a former IDEO designer, and Orchestra co-founder Scott Cannon, who was a Mac and iPad operations team leader at Apple, took Mailbox to Dropbox just one month after its launch.
mailbox-desktop-8316-002.jpgMailbox desktop beta for Mac. Josh Miller/CNET

"Arash [Ferdowsi] and Drew have a penchant for intuitive simple solutions," Underwood says. "One of the key differentiators that made Dropbox successful was this intuitive experience: just another folder on your computer, yet another folder that had these magical properties.

"That transformation...it takes a lot of design to get to that place where it just seems like an obvious solution," he added. "Simple design is surprisingly complicated to pull off and it actually takes a lot of design work." In Dropbox, Underwood says he saw a company that is striving to impact people's lives through productivity, just like Orchestra set out to do.

"For somebody that came from the outside walking in, Mailbox does not feel like Mailbox grafted inside of Dropbox," says DeVincenzi, who joined the company in November and is part of a team of around 30 employees that works the email service day-to-day. "It just feels like a continuation of Dropbox. It feels fluidity integrated into what's going on here."

The undercurrent channeling between Mailbox and Carousel -- which were only designed with similar philosophies and not with a consistent visual style -- is emblematic of Dropbox's refined approach with Underwood in the mix. "In the mobile era, the apps that win are the ones that are less like a Swiss army knife and more like a hunting knife," Underwood says. That penchant for focused simplicity is a trademark not just of Dropbox, but of many of the breakout mobile and desktop productivity hits of the last few years.

"I would say it's about the essentials," says Jeremy LeVan, the designer and co-founder of the mobile and desktop calendar service Sunrise.am. "That's the beauty about designing for a calendar or email, things that have been around for a while. Everyone relates to a calendar and everyone knows what it's about, yet you have to be careful about how you design it and how you cage it. It's not something everyone will understand."

Stewart Butterfield, the co-founder of Flickr and creator of the fast-growing office communication service Slack, expresses a similar philosophy when it comes to product development.

"I think the design makes a difference," he told CNET in an interview last week. "There's a set of features that people want that they don't even know that they want. They weren't asking of them. But when they get them, they like them." That kind of Apple-esque approach -- giving users what they need even if it's not what that initially want -- is how apps like Mailbox help change our behavior for the better in the eyes of its developers.
"In the mobile era, the apps that win are the ones that are less like a Swiss army knife and more like a hunting knife."
Gentry Underwood

"It puts us in a position where we have to be a little more opinionated about some of the constraints we choose to impose on the product," says DeVincenzi, "so that it does not end up being a bloated, can-do-anything, does-do-everything sort of product and more like a focused experience. Getting there just required saying no to a lot of things." Initially, that included email labels and drafts. The former is on its way, while drafts are in the latest Mailbox for desktop beta. But labels were initially excluded, Underwood says, because they wasted people's time when an email client's search function is a better way of finding what you need.

"The core goal we're trying to do is help people get this feeling of having this elephant on their back off. A lot of people...are wasting a lot of time organizing and not using," Underwood says. It's the very same tactic, he points out, that Apple employed with natural scrolling in its desktop OS so that using an iPhone and iPad with your fingers mirrored the direction of your laptop trackpad or desktop mouse on a Mac. That, though, was a choice and Mailbox, now more resource-heavy, can afford to hand choices to users instead of putting the functionality on the back burner.

"Mailbox needs to evolve to that place. There's enough real reasons for the support of labels that eventually we need to support labels. It's just a question of prioritization in terms of product development," he says.
Seeking the pain

Dropbox has yet to identify its next target, the problem for which it will identity a solution and roll out an app that can join Mailbox and Carousel in the unified language of focusing, as Underwood says, on one thing and doing it very well.

"To me, the most interesting, most ripe areas for innovation center around working together as teams, collaborating in a world where some people are on their computer and some are on their phone," Underwood says. That's a world that, like Dropbox's core file service, stretches far beyond the tech industry. As Houston once pointed out, "You think about who needs Dropbox and it's just about anybody with a pulse."

A communication tool would also mesh well with the company's current collaboration focus aimed at Dropbox for Business customers. Alongside the Carousel announcement in April, Dropbox announced Project Harmony and a partnership with Microsoft to bring real-time file changes to Microsoft Office projects like documents and PowerPoint presentations. Continuing to beef up its enterprise offerings could only aid Dropbox as competition with Box, currently on a path to its very own IPO slated for later this year, only grows fiercer.

To that end, Underwood sees the hodgepodge mess of chat, email, Google Docs links, and even Dropbox folders as a "zoo, a big mess that is ubiquitously a mess." It's bad enough on your computer, he says, but "God help the person who tries to do that on their phone."

"I am very attracted to the idea of building tools that are so useful around that space that teams say, 'How did we do this before? Do you remember how crazy that was?'" Underwood says. The goal would be to give business customers something so valuable that it would give them an immediate edge over their competitors. There's only disparate indications of what that looks like now -- Butterfield's Slack software is the closest we have to an organically popular team collaboration tool, yet it specializes mostly in chat.

But doing it to the tune of Dropbox's hundreds of millions of users would be "big world impact" stuff, the very same efficiency multiplication that cloud syncing packaged as a magic folder helps propagate.

"That's the kind of thing," Underwood adds, "is worth putting your time and energy into."