Illustrating a more human brand (part 1)

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.

Illustrating a human brand by Brandon Land

In December 2016, I received the honor of leading the Dropbox illustration team. My first goal has been to understand the decisions that were made to cement Dropbox’s artistic legacy. As the illustration team looks forward to evolving and pushing the brand forward, I think it’s important that we understand the legacy and carry it with us while we advance. In preparation for this historical recollection, I had the pleasure of interviewing some of the influential creative minds that helped define and prove illustration’s heavyweight status. Through these interviews, I found a powerful story about taking giant leaps of faith against opposing ideas and data to prove the power of illustration.

In the beginning, fast and cheap win

First illustration drawn for Dropbox by Jon Ying

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. If they didn’t trust that Dropbox was going to take care of their needs, they were out. The drawing could actually cost the company. However, Jon believed simple universal drawings connected on a human level and inspired empathy when things might not be working right. He believed it could even help retain customers through some tough times.

“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

Arash and Jon’s passionate vision was met with extreme doubt. There were just no data or examples to support that the style would be a good decision. At face value, what Jon Ying was asking was pretty nuts. If you can think back to nearly a decade ago, no one was using illustration in brands like Dropbox, especially not stick figure comics. Drew Houston (CEO and co-founder) had good reason to think it was a silly idea. But that’s the thing: it was a silly idea. It didn’t take itself too seriously. It wasn’t beholden to corporate trends or best practice marketing and sales knowledge. It thumbed its nose at being put in a box.

Illustration by Jon Ying
Illustration by Jon Ying

What the style did have, however, was a well-reasoned argument for why it would work. Jon’s solution worked well for the biggest realities Dropbox was facing at the time. The product was young, it went down almost daily in 2008, and the team needed a quick and easy way to communicate with customers in a way that felt like there were humans working on the problems. At the time, Dropbox couldn’t afford an illustrator, and there was a need for a lot of communication at the time. Jon explains, “There actually wasn’t much inspiration or thought that went into the early day illos. They were in many ways driven by necessity, chance, then reflection.” In those days, debate about using stick figure drawings often resolved itself through the classic engineer’s agreement: try it, and if the data didn’t support it, they wouldn’t do it again. Fortunately for us, people really responded to Jon’s work. They even went so far as to take time out of their days to email about the drawings. It was a hit!

“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

As the need for illustration grew, one of the next challenges was to draw something for the 404 page. This would be the first introduction of illustration inside the actual product. The only problem was that Jon didn’t have any drawing supplies other than plain ol’ pens. Arash decided the two of them would go to the Walgreens downstairs and buy some art supplies. They picked out some colored pencils and drawing paper, and voilà, the Dropbox aesthetic was born. Jon drew a version of the Dropbox logo à la Escher, and it was a big hit internally. However, despite internal praise, there was another roadblock for Jon to overcome. Creating silly drawings on the blog or in emails is one thing. But putting them in the product? That’s crazy talk! Convention was loud and clear that this color pencil drawing of insanity was an unprofessional approach. 404 pages are a moment of frustration, and Jon was making a joke? The challenge had to be raised again: “Do we want to be a company that does this kind of crazy stuff?”

“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.”

As the style progressed, one of the main components of meaning for the work was to connect with people in a more personal way. Jon started to build a means of conversation within his work by using Easter eggs in the product. These little moments of discovery made people say, “Oh, that’s clever.” And more importantly, it invited them to think, “I’m clever for getting their reference. I relate to the people who work at Dropbox.” Jon had started building relationships and friendships with people through his art. There were even times when strangers literally walked up to Dropbox employees on the street and gave them a hug. That type of relationship was traditionally considered impossible to create with a company.

Version history by Jon Ying

Jon’s philosophy didn’t just stop at an emotional connection. He also built out a philosophy for the thinking behind the work. Jon wanted Dropbox’s users to understand the imaginative journey one must take to build this type of product, and how hard Dropbox employees worked to make it a reality. Dropbox needed users’ trust, and that meant sharing a piece of Dropbox’s culture with them. To do that, Jon devised a fantasy world where metaphor and pop culture collided to put a fun spin on what was ultimately an extremely boring concept — cloud storage. When the need arose to communicate about version history, Jon could use a DeLorean from Back to the Future. When talking about mobile capabilities, Jon would show characters enjoying life with all their files in a kite. He crafted compelling reasons around the use of illustration, so illustration would be in a solid position the next time it was second-guessed.

Illustration by Jon Ying

Jon contributed many conceptually interesting illustrations, but he is the type of guy who loves to take a new thing head on. Soon enough, he became involved in too many parts of the company to keep up with the illustration work needed. It was time to hire some new talent. In a serendipitous series of events, Dropbox had recently contracted Ryan Putnam to build out a design/illustration system for their big DBX event. His work was amazing, and Dropbox decided to bring Putnam on board to help with the giant mountain of work. This is the beginning of what has fondly been referred to as the “Putnam era.”

Systemizing aesthetics and the feedback process

Illustration for DBX developer’s conference by Ryan Putnam

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. People aren’t afraid to make mistakes. They’re encouraged to move fast and learn quickly what does and doesn’t work. The tough part managerially is that everyone’s opinion on everything is valid. For illustrations, this makes for a lot of, “We’ll know it when we see it.” That means every illustration becomes a monumental effort of meandering through the darkness. Illustration transforms from a delightful part of the brand to a battle zone of opinions. This is the chaos that quickly started to manifest around the time Ryan Putnam joined the team.

Cupcake illustration by Ryan Putnam
Illustration by Ryan Putnam
Illustrations by Ryan Putnam
Illustrations by Ryan Putnam

Putnam was a generalist, which was perfect for Dropbox at the time. He designed and illustrated for products, marketing needs, blogs, internal comms, etc. The sheer volume and variety of the design work needed was pretty staggering. Putnam needed to move quickly, so he leaned on an illustration style he was most comfortable with. Putnam’s style was warm and approachable. It was a logical evolution for the Dropbox brand, but at the same time, designers Alice Lee and Allison House were also creating illustrations in their own styles. There was a moment in time where work was made in any style an artist wanted. There was minimal oversight because there was so much to be done. If it felt good enough, it made it through. There was a lot of talented people creating great work. But as it turns out, that’s not a sustainable model for a brand. If anything goes with the illustration, then anything also goes with the feedback, and chaos started to take root.

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

Putnam saw the writing on the wall. Illustration needed to be systemized, or it was going to be replaced. He dedicated his tenure at Dropbox to building a guide for how illustration was created and measured. This included a specific point of view on how the company gave feedback about illustration. It turns out that a lot of meetings go into educating people about brand best practices. Like, a gross amount. And on top of those meetings, Putnam and the team still had to get their actual design work done. At this point, Putnam started walking the same path that Jon Ying had to pave in the beginning. To ensure illustration’s place in the brand, they had to work twice as hard.

Illustration by Zach Graham
Illustration by Zach Graham

Putnam started exploring an aesthetic system that could be scalable as they hired new designers. He understood that in order to scale their team, a foundation needed to be created for illustrators to work on top of. Dropbox brought in illustrator/designers Zach Graham, Justin Pervorse, and Linda Eliasen to help scale the design language. Ultimately, Zach and Putnam dedicated their focus to creating an updated brand style that honored Jon Ying’s style while also evolving it into a more refined digital style. They created an easy-to-replicate system of using objects to tell stories. Often the objects had smiles. Zach jokes, “At one point, I think everything had a smile.” People tend to give a nostalgic self-aware laugh at the smile period. There was a real mandate for the illustrations to convey delight. There was a lot of delight. 😀

Illustrations by Ryan Putnam and Zach Graham

The emerging system was working. They started scaling it out to other products and pressure testing it as a broader language. Putnam was able to build a precedent for the work that served as common ground for feedback and furthered illustration’s role in the company. This was a major win for the company’s ability to understand and communicate ideas through illustration. There was one big issue, though. Through the process of systemization, the style had lost a key component. It lost its whimsical, conceptual nature. Where Jon Ying once strove to never show a folder or file, the style now was primarily object-based.

Design and illustrations for Dropbox’s now retired product Carousel.

The contrast between a more objective style and purely conceptual pieces is very interesting. In Jon’s days, the product was very conceptual. The user’s stuff was now in the cloud. People didn’t even know what “the cloud” was. It was brand-new, and the company needed to sell why this was something worth moving toward. It was closer to a lifestyle connection. Whereas during the Putnam era, people understood the cloud, but they needed to understand the practical uses of Dropbox. This meant that mentally connecting one’s environment to Dropbox was helpful in showing its usability. But ultimately, one or the other wasn’t good enough for the team. They constantly thought about what was working and how to take it to the next level.

Proof of concept

Access denied illustration by Zach Graham

While Dropbox was growing rapidly, new hires were brought in from a variety of other successful companies. Leadership got deeper and wider, and illustration had a new crop of people to prove itself to. The new illustration system was working, but so much changes quickly in startups. They have to zig and zag constantly. This meant new hires across the company could only use what they had learned from other companies to inform what should happen at Dropbox. After all, they were hired for their past successes. The only problem was that Dropbox wasn’t like any other company. The people that joined Dropbox wanted to work there because it has a certain je ne sais quoi, but they had a hard time translating that internal culture to how the brand should sit in the world. The company had gone full circle, and illustration was up for another round of “survive the chopping block.” Some believed deeply that it was time for Dropbox to feel more in line with what other companies were doing. The problem was that most companies relied heavily on pictures of boring people just looking at their phones in a work scenario. Lame!

Fish bowl illustrations by Zach Graham

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. At that time there were smiley faces on everything, and I didn’t want to do that. I didn’t want to draw a file crying. It wasn’t going to work.” Zach came up with the idea of two differently sized fishbowls. He portrayed the concept of space without connecting it to files at all. He wanted you to remember how sad your pet would be if they were in a cramped space. You don’t want to be the type of person that lives in a cramped space, right? Apparently, people can really relate to the emotions of a fish, because it convinced people not to click that final “Yes, I’m sure” button. Some say this illustration saved the company millions of dollars. Others say, “Whoa, cool, people say it was that much?” Either way, I wasn’t able to track down the actual statistic for its success, but its impact on the future of illustration was quite significant.

Illustration about building on top of Dropbox by Zach Graham

While the fishbowl pieces served as the sacrificial lamb on the chopping block, the big debate about if we should move away from illustration roared on. Illustration had proven itself useful in certain battles, but there was still the question of whether it was the right tool to win the war. “The sentiment was that the company needed to grow up,” Zach recalls. “I agreed with that sentiment. We did need to grow up. But illustration can be conceptually sophisticated, and that’s what I was interested in.”

Illustration by Zach Graham

At the time, it was difficult to find the right answer between both sides. Although there was a tighter system for understanding illustration, there was no clear way for other parts of the org to understand what brand was or how it should be approached. There wasn’t a brand team at the time. There was just a pool of designers working on pretty much everything. While Zach’s conceptual illustrations were still proving their worth on the growth and monetization side, it started to become clear that there needed to be a defined process for making brand decisions. The contrasting ideas about illustration’s worth were not going to solve themselves.

“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…


Update: Still feel the need for more juicy illustration history? We published part two here.


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