Dropbox Design
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Dropbox Design

Illustrating a more human brand (part 1)

The history of Dropbox brand illustration

Illustrating a human brand by Brandon Land

In the beginning, fast and cheap win

First illustration drawn for Dropbox by Jon Ying

“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. People started writing in and tweeting to apologize for hurting us by leaving. Many even resubscribed.” –Jon Ying

In the early days of a company, these decisions can become hard to untangle, as it’s often two heartfelt, passionate beliefs pitted against each other. This decision was hashed out in an absurdly unconventional way. It took a long, drawn-out Dance Dance Revolution battle between the two founders. It lasted 23 hours straight. No sleeping. No eating. No bathroom breaks. No mercy. Ok, not really — it was actually just a meeting, but in that meeting, co-founder Arash Ferdowsi passionately fought for Jon Ying’s vision. He believed Jon was on to something. After all, in the early days, Jon worked in customer support. He was the most connected to the users, and Jon was damn good at connecting with an audience at a universally human level.

Take your stuff anywhere by Jon Ying
Keep your files safe by Jon Ying
Illustration by Jon Ying
Illustration by Jon Ying

“Dropbox’s brand thinking at the time was, should we try doing the gradienty bullshit every other 2008 tech company is doing? No, it’s lame. Should we try hiring a full-time illustrator? No, we’re poor. Should we just stick with this style for now? Yeah, Jon seems to draw clever stuff, it works with the product experience, and we can keep paying Jon the same money for doing two jobs. What a schmuck.” –Jon Ying

Psychobox illustration by Jon Ying

“The early days were all about irreverence. It worked for our users, but perhaps more importantly, it attracted the type of employees we wanted at the time. An illustration of a raptor, eagle, and shark was used on our jobs page. Many of our early hires went on to say ‘your jobs page was different from every other one out there, and I saw myself being a part of what you were trying to do.’” –Jon Ying

At this point, you probably see a pattern here. A desire to be innovative or different will always meet its counter argument to do what is expect and tested. This debate will go on in every company throughout time. However, Jon wasn’t disheartened by the debate, and he didn’t take his initial wins for granted. He understood illustration would be continually on the chopping block, so Jon took every chance he could to build meaning and value around the work that he did. “We weren’t simply being irreverent for irreverence’s sake,” Jon remembers. “There were other factors of familiarity and approachability that we wanted to capture. A kind of a ‘you can do it, too’ spirit we wanted the user to feel.”

Version history by Jon Ying
Illustration by Jon Ying

Systemizing aesthetics and the feedback process

Illustration for DBX developer’s conference by Ryan Putnam
Cupcake illustration by Ryan Putnam
Illustration by Ryan Putnam
Illustrations by Ryan Putnam
Illustrations by Ryan Putnam
Illustration system design by Ryan Putnam

“Putnam is a real class act. One gets very few opportunities to work with someone as thoughtful, kind, and hardworking as him.” –Jon Ying

Where Dropbox’s illustration once had a focused point of view, it was starting to jump all over the place. It started to seem like an afterthought as opposed to something deeply integrated into the company’s DNA. Putnam understood that if an illustration system lacks a strong point of view, then everyone and their dog will impose their uninformed opinions. This was causing chaos where a single piece of feedback could set projects back or even derail them completely.

Illustration brand guidelines by Putnam
Illustration brand guidelines by Putnam
Illustration by Zach Graham
Illustration by Zach Graham
Illustrations by Ryan Putnam and Zach Graham
Design and illustrations for Dropbox’s now retired product Carousel.

Proof of concept

Access denied illustration by Zach Graham
Fish bowl illustrations by Zach Graham
Illustration about building on top of Dropbox by Zach Graham
Illustration by Zach Graham

“What we saw that marketing didn’t see yet was that illustration was starting to become really popular in brands, and as it was emerging, people were already ripping off what we are doing. It was obvious that we were doing something right. So we wanted to push that.” –Zach Graham

Every pillar of the company had specific needs, and there wasn’t a clear path for anyone to work alongside brand experts to create meaningful work for those needs. They didn’t understand that a brand’s major power was that it could make hard-to-understand concepts relatable at a gut level. Without brand, decisions boiled down to the hard numbers and research coming from marketing and finance. It’s hard to beat those numbers with a mere, “Trust me, this will work.” It’s easy to blame one side or the other for the rough patch in the relationship, but really both sides were 100 percent right in what they were trying to do. They all wanted what was best for Dropbox. The real problem was that there was no organizational structure around how they could build a brand correctly. Perhaps even more importantly, there wasn’t anyone dedicated to educating people about the long-term powers of the brand as a whole.

“In-the-moment decisions often have a disproportionate impact on the future. Drew could’ve said no to psychobox. Ryan Putnam could’ve not drawn the cupcake. We could’ve gone with colored geometry over broken line. We could’ve switched 100 percent to photos. But maintaining our illustrations’ essence is a deliberate tradeoff we’ve fought for, because it’s the closest proxy in our brand for the wonder and joy people feel when they accomplish things with Dropbox.” –Jon Ying

As with all good two-part stories, I must end part one with a cliffhanger. Will our illustrative do-gooders be able to find a better way of working? Is illustration at Dropbox doomed? Tune in next time as I tell the tale of the creation of the brand studio, demanding bosses, and a whole lot about the conception of our modern-day Dropbox illustration style. There might even be Razor scooter battle on the stage of the SF Opera! I guess you’ll have to wait and see…

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