Dropbox CEO Drew Houston on its new mission to sync your work (1/2)

Many of us are familiar with Dropbox as a convenient way of keeping files in sync across the multiple devices we use in our digital lives. Now Dropbox is taking on a much bigger challenge — helping us keep our work in sync across all the digital teams we're a part of. I sat down with Dropbox CEO Drew Houston for an exclusive diginomica interview in the company's San Francisco headquarters earlier this week to find out more about this big step in Dropbox's evolution. It's "a big opportunity," he says, but also a new departure:

This is step one of a very long journey — in many ways, a new beginning for us.

At first glance, the new product conforms very closely to the collaborative canvas that I mapped out a couple of years ago as the ideal framework for teamwork in the digital enterprise. My first impressions are therefore positive — this has the potential to make a huge impact. But when I met Houston I had three questions front-of-mind about the challenges Dropbox will face in bringing it to market:

• Adoption — how to ensure users understand how to use the product effectively?
• Credibility — how to persuade CIOs that Dropbox is not the consumer tool they thought it was, and see it as an enterprise tool?
• Co-opetition — how to maintain essential partnerships with the likes of Microsoft, Google and Slack, while at the same time aiming to supplant them as the go-to platform for team collaboration?

We'll come to the responses to those questions in part 2 of this two-parter. But first, here's a bit more detail about the new product and how it came about.

From 'magic folder' to 'magic workspace'

The new Dropbox application lives on the PC or Mac desktop, and retains the folder metaphor that's familiar from the traditional view (which remains available) in Explorer on the PC or Finder on the Mac. But instead of showing only local files, it will now be possible to add G Suite and Office 365 files and open them directly from the folder, as well as links to web pages and online resources such as Trello boards. Users will be able to add a description to the folder, and can 'pin' important items at the top of the content list. Crucially, search now scans across all of the files and resources included in the folder.

New features designed to support team work include the ability to easily add people to a folder or at-mention them in comments or workflow. A side panel that's previously been available only in the web app shows activity streams and comments. There's also tighter integration with applications such as Slack and Zoom, such as sharing a file to a Slack channel directly from Dropbox, or opening a file directly from the folder to view in a Zoom meeting, with more integrations to other applications coming soon.

All of this functionality is in response to watching how people's use of Dropbox and other collaboration tools has evolved in recent years, Houston explains:

Dropbox has always had this metaphor of the 'magic folder', and that served us really well. But when we watched what people were doing, over the years, and certainly in earnest in the last few years, people were really using it as a 'magic workspace' ...

It's actually a relatively new problem, where we have all these different apps and ecosystems, and we need to work seamlessly across them. And none of us, no company, no end user, is truly in control of their environment anymore ...

So in the last few years, we became entirely focused on productivity and collaboration, because the opportunity we saw was, this experience is getting a lot more distracting, and fragmented. And every company is working on polishing their tool or their little piece of it, but nobody's really looking at the system.

Bringing it all together

While the result looks simple and obvious on the surface, it's taken a huge effort behind the scenes — Houston calls it "a seismic retrofit" — to bring everything together:

The engineering it takes to stitch together all these different [elements] to do this seismic retrofit on the file system — to enable it to handle all of these 21st-century concepts, not just real-time collaboration, but comments and at-mentions and all the basic things that the consumer world has made commonplace — is a big undertaking, because we don't actually own the operating system.

Now Dropbox has the huge job of persuading its user base to switch to this new way of working. One of the most important factors there has been making this an easy, incremental step to take, says Houston:

We want to be very thoughtful about how we roll out a change like this. The good news is, the file syncing metaphor, the operating system integration, none of that changes. However you were using Dropbox yesterday, you'll still be able to use it tomorrow the same way.

Of course we're introducing this desktop app, which hopefully, people see what we see, and they'll realize like, 'Oh, yeah, instead of our files and cloud stuff being on different planets, instead of having to toggle back and forth hundreds of times a day, it'd be great if this experience were integrated and coherent, and designed as if one company had built all these things' — while also maintaining the freedom of choice.

Continue to part 2 for Houston's thoughts on driving user adoption, changing CIO attitudes and working with competitors.