In UX Evolutions, we will be exploring how the user experience (UX) and user interfaces of some of the most prominent online services have changed over the years.

This time, we’re looking at how the wildly popular file-hosting service Dropbox has evolved. The concept came about when MIT student Drew Houston regularly forgot to bring his USB flash drive with him. Instead, he started creating a solution where he could have remote access to them. He partnered with fellow MIT graduate Arash Ferdowsi and founded Dropbox, which has gained well over 500 million users since its inception in 2008.

We talked to Adam Polselli, director of design at Dropbox, and Yi Wei, staff product designer at Dropbox, about design challenges and considerations, the role of user research, the recent bold redesign, and more.

What was Dropbox’s user experience like at the very beginning, in 2008?

Yi: Dropbox was just a folder, and we had a webpage that was pretty basic. You could access your stuff from a computer, but that was really it. What we were trying to strive for at the time was ensuring we create the same level of trust and expectation that people have for files on their computers. We didn’t want to introduce anything new to the experience that was unexpected. If it looks like a file and if it looks like a folder, then it should be a file and a folder.

One of the first website designs for Dropbox's homepage.
One of the first designs of

How has the UX changed over the years?

Adam: A lot of it hasn’t changed. It’s still about integrating really well with how people work. A principle we held onto is making sure that Dropbox feels really simple and intuitive and fits into your workflows.

Our user interfaces and experiences certainly have evolved and opened up over time. Dropbox is more powerful than it was back in 2008. A challenge that we’ve faced is how to continue to introduce new features and make Dropbox more powerful without making it more complex. So throughout the design process, we’re really mindful of making sure that we have things like smart defaults that don’t add a lot of complexity or don’t force users to make a lot of decisions. We think about building a product that’s really simple but also flexible enough to support the needs of millions of different people all the time.

Yi: One way to think about the evolution of our design is to think about the evolution of the types of problems that we are trying to solve. In the beginning, it was very focused on backing up content, making it available in different places, and sharing it with other people. Now there’s a new class of problems around workflows, different devices, different types of files, etc. So we’re trying to stay true to our principles of simple and intuitive while making sure we’re actually solving those problems.

What are the main considerations in evolving the UX of the product?

Adam: A lot of companies, once they reach a certain scale, start to invest in design systems, which are essentially reusable patterns and components that allow you to build more consistent products. That’s really important, because a lot of our customers use Dropbox on their desktop, on their phone, on the web, depending on their workflow and where they are. We want to make sure that they can move seamlessly from platform to platform, and one way to do that is to ensure that the experience is consistent across each of these platforms. So you don’t have to relearn the product, whether you’re trying to share something from your computer or from your phone.

Various dropbox redesigns
Dropbox redesign. Image by Dribbble.

What role does user research play in the design process?

Yi: It’s incredibly important. Because we’re trying to focus on user problems and solving them, we need to have the knowledge of what people are actually doing. What are their motivations, what are their goals, and needs? But it’s not just usability testing for us, and it’s not enough to just have a solution that people don’t get confused about.

What we really want to do is improve the current state of the “art of work” for people. We’re doing a lot more forward-looking things, especially with our new mission of designing a more enlightened way to work. How can technology guide people? We’re using user research in our strategy to inform the direction that the company and our product should be heading toward.

dropbox save box
Dropbox redesign. Image by Dribbble.

What was the thinking behind the bold redesign you rolled out late last year?

Adam: There were a lot of motivations for the redesign. As Dropbox has evolved, we didn’t feel like our brand any longer reflected the way that we saw ourselves and the role that we want to play in making work lives better. There’s been a tremendous effort by lots of teams at Dropbox, including our brand team, and it was really about understanding how to better tell our story to the external world.

dropbox redesign
Dropbox redesign. Image by Dribbble

We want people to think about Dropbox as a tool that fosters creativity and allows them to do work that matters and be productive. The rebrand was deliberately provocative because we really wanted to differentiate ourselves from the standard message that’s out there about increasing team effectiveness and team productivity. A lot of our research showed that people don’t use words like productivity, effectiveness, and speed when talking about what they want from their tools and what they dream about or aspire to be. They talk about why they did the work that they’re really proud of. They talk about wanting to have time to focus on what matters.

What’s next for the Dropbox UX?

Adam: We’re spending a lot of time thinking about how to bring our mission to life through our product. We have a mission to unleash the world’s creative energy by designing more enlightened ways of working. We’re being really thoughtful about what that means for the software that we build. One example is that we really want to build tools that foster focus and foster flow. Lots of research and data coming out these days shows that the modern workplace is a very distracting place and people spend a ton of time doing work that’s really draining and not really satisfying — all these things that we describe as “work about work.” We want to build a tool that eases all of that work about work so that you can spend more time doing work that really matters to you.

We want people to think about Dropbox as a tool that fosters creativity and allows them to do work that matters and be productive.

Adam Polselli, Director of Design at Dropbox

It’s been interesting to think about what that may mean for the software that we build. For example, a lot of modern software technology will leverage notifications as a way to drive adoption and retention. I think there’s a tension in there, in that notifications are also a way to really distract people. If you’re sitting at your computer, and you’re getting a notification every few minutes, and someone mentions that someone needs something from you, we will have fostered the environment that makes it really hard to do focused work.

screenshot showing various dropbox pricing
Dropbox redesign. Image by Dribbble.

Yi: The classic tools today mostly allow people to perform the thing that they can already do, but faster. But all of us strive to create something of higher quality and improve the way that we think. The challenge of Dropbox, and of all technology right now, is figuring out how to create technology that helps us think better and learn. For example, there’s a lot of information about the efficiency and effectiveness of the hamburger menu. Right now, it requires a designer to go online or have a mentor to understand it. What if technology, the tool that you’re using knew you’re using a hamburger menu and gave you the pros and cons. All of a sudden, the tool itself has given you a self-critique that’s enabling you to think better. That’s the new realm.

Read more UX evolutions for Netflix, Medium, Firefox, Etsy and Gmail.