Illustrating a more human brand. The history of Dropbox brand illustration.
For years before I joined the Dropbox illustration team, I assumed the Dropbox illustrators had it easy. I imagined talented people getting to make great work for an organization that believed deeply in the power of illustration. I mean, what could be chiller than drawing all day? To a casual observer, it’s easy to take for granted the pioneering role Dropbox has played in brand illustration. But over the last ten years, there have been a handful of times when illustration as a Dropbox hallmark has been in jeopardy.
It took nearly eight years of speaking up in meeting rooms and drafting late night email essays to fight for illustration’s power. This is because illustration has long existed at ground zero of Dropbox’s identity crisis: are we consumer or enterprise? Do we speak to those audiences in different ways? It’s a historic tension that still hovers over our illustrators today.
In the beginning, fast and cheap win
Illustration at Dropbox comes from very humble beginnings. Jon Ying, who does not consider himself an illustrator, drew a piece for a blog post about some bugs they were working on. The image portrayed a stick figure chasing after a bug with the intent to smash it to oblivion, and it sparked an intensely debated existential question for the company. Who are we? Should we be just like all the other respectable companies and play it safe? Or should we try something interesting and make a statement? The decision to publish the stick figure wasn’t easy, but it was an important decision. Users can be fickle.
I made a drawing for an email campaign sent to people that recently downgraded from Dropbox Pro. The image we made was a weeping PC with a thought bubble with a broken heart inside.
Dropbox was growing very quickly. The product was a budding success, and the need for talent was massive. If you’ve never been part of a small company that’s rapidly growing, let me take a minute to describe it to you. It’s insanity. Every task, job, problem, success — it’s all brand-new to everyone involved. The entire company is making educated guesses while taking on responsibilities they never thought they’d be able to effectively help out on. This type of growth is a key component to the revolutionary success of the tech industry.
Proof of concept
Illustration had to step up its game. It had to serve as an emotional connection that far outweighed what other companies were doing with photography. One chance to prove that emotional power arose with the need to create a “please don’t downgrade” page. The illustration appeared when users wanted to downgrade from a paid plan to the free plan. Dropbox needed something to help users understand they get a whole lot of bang for their buck. Zach explains, “I wanted to figure out how to make people feel guilty without being an asshole.