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

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

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!

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

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

Systemizing aesthetics and the feedback process

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.

Illustration for DBX developer’s conference 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

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

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

Growing beyond simple beginings

Our ragtag band of illustrators was fighting the good fight to create delightful work for the Dropbox brand. But as the company grew, it became more and more difficult for many to understand the role of brand designers and illustrators. After all, at that time there were no “brand designers” by title at Dropbox. There was no one whose role it was to be an evangelist educating people about the need for well-thought-through brand strategy. It all felt very fake it till you make it.

I think it’s important at this time to quickly zoom out on the history of in-house brand designers and illustrators. Many young designers might not realize that working as an in-house designer used to be its own kind of hell. I believe Dante would have created a special ring for it had he lived in this day and age. For decades, in-house designers were faced with the Sisyphean task of trying to make work for vague marketing needs created by business-type folk who spouted art direction based on their whopping zero years of design expertise. The idea of design thinking or problem solving was nowhere to be found inside most companies.

“Many young designers might not realize that working as an in-house designer used to be its own kind of hell. I believe Dante would have created a special ring for it had he lived in this day and age.” –Michael Jeter

This new world where it’s prestigious to be a designer at places like Facebook, Google, and Dropbox only sprung up around 5–8 years ago. A new trend of “design-centric” companies started to emerge. It was a promising new philosophy for companies that wanted to be user-friendly and forward-thinking. However, even though the concept of “design-centric” became a buzz term in Silicon Valley, many companies don’t understand what it means or how to implement it as a core principle.

Dropbox happens to be one of the companies that leaned on design as a core principle pretty early on. But even still, the idea was in its infancy in the corporate world. This meant they had no choice but to figure it out on the fly, which is anxiety-inducing, to say the least. And even still, some folks were yet to be convinced of this new philosophy of giving art nerds a seat at the table. I mean, let’s be real. There are a lot of weird eye-roll-worthy trends that crop up here in California. So it’s understandable that some would be skeptical.

For in-house designers at Dropbox to keep everything from going pear-shaped, they had a lot of organizational maneuvering to make sure everyone was on board with this atypical brand they were building. Brand design is hard to understand and is rarely measurable in the short term. And on top of that, it only tends to work when it’s bold and takes self-assured risks to be authentic and unique. That type of vulnerability is hard enough at a personal level, let alone when your job is on the line and your company is growing by leaps and bounds.

*“This new world where it is prestigious to be a designer at places like Facebook, Google, and Dropbox only sprung up around 5–8 years ago.” *–Michael Jeter

Ok, so why am I going on and on about my view of what it used to be like to be an in-house designer? Well, I think it’s important context for the time-traveling journey we’re about to take. Dropbox, like every company at the time, had some serious growing pains to get through. The Brand team had to prove it deserved a seat at the table. And as a company’s needs are constantly evolving, Brand must always be aware of where they can add value. This constant pressure is why brand designers are passionate, dogged, and sometimes downright confrontational about their ideals. And this fighting spirit has ensured that Dropbox gets to count itself as one of those great design-centric companies.

Below are some of the key projects that the brand illustrators were fortunate to be a part of. There were, of course, many other things going on for the Brand team as a whole, but we’ll stick to illustration, as the stories of the entire team would fill up another two-part Medium post.

The Creation of the Dropbox Brand Studio

This is where a new character joins our story: a creative leader well-equipped to lead the team on the quest for keeping the Dropbox brand inspirational. Kristen Spilman, previously an associate partner at Pentagram, joined Dropbox to build a strong, scalable brand. Her entire career was built around the power a brand holds. She learned from and worked with some of the best of the best. The true design geeks on the Brand team became giddy with anticipation.

*“Kristen came from the design heavyweights, so she brought a legit nature to the team because she rubbed elbows with the design royalty. We would incorporate her feedback, and things always came out better even if at times it was difficult.” *–Zach Graham

Kristen’s first initiative was to build a separate arm of the Design org that was specifically working on brand work. She separated brand designers, writers, and illustrators from product design, which helped both orgs increase focus and expertise in their respective fields. Zach Graham, with the addition of three new illustrators, Brandon Land, Fanny Luor, and Dominic Flask, started to work on elevating the brand along with their shiny new team. First impressions can make all the difference for audiences evaluating a product. With this in mind, the Brand team focused their efforts on redesigning the home page. It desperately needed an update, and this was the Illustration team’s chance to come up with a new style and system for illustration.

“There were many reasons why we needed a new illustration style, but one of the most pressing ones was for scale. The role of illustration was prevalent in the product, the product was expanding, and historically, the illustration work had always been created by a single person, be it Jon, or Ryan, or Zach. The demand was growing and the illustrators were burning out. I needed to grow the team and ‘scale illustration’ so that we could meet the needs of the growing product, update our voice to feel current, and build a system with constraints so we could scale with consistency.” –Kristen Spilman

This all sounds exciting, right? But there’s something they don’t tell you about brand illustration. The process of creating a new illustration style is an excruciating one, especially when it’s coupled with something so politically heated like the redesign of the home page. The new style had the potential to be anything under the sun. It could have been 3-D, geometric, analog, vector, etc. Everyone had opinions about it. How the hell do you decide which direction to go? There’s no way to measure, test, or research in any meaningful way. In many ways, it’s a subjective pursuit led by intuition and gut. Don’t screw it up, team!

“Kristen really shielded us from a lot of the politics and negative feedback. She didn’t want the pressure of the world we were in to harsh our creative.” –Brandon Land

Projects like this tend to create a bit of a competitive frenzy if your team is full of talented, hardworking people who want nothing more than to prove themselves. And that’s exactly what Dropbox had. This was a chance for the Brand team to make their mark. The stakes were high. If there were places where the internal team was struggling, then the Brand leads would hire outside help to come mix up the process. Some illustrators worried about the final aesthetic that was to be chosen. What if it was something outside of an illustrator’s wheelhouse? Would they be axed? These were some of the fears and motivators creating a pretty intense moment in time.

With healthy competition in mind, the illustrators set off on their own to concept and iterate.

Concept exploration by Zach Graham

Zach Graham started to zero in on a concept based on the building blocks of creativity. He was using basic geometric shapes to form larger ideas together. These ideas relied heavily on motion to communicate. He also explored an interesting idea he called “monumental scale.” This idea was based on the concept that devices were large enough to contain or capture people’s life adventures.

Your stuff lives here by Brandon Land

Brandon Land was pushing a concept of everything being connected by exploring how to use a line that threads everything together. This idea was built on the concept that Dropbox brings all your files together and lets you connect them with anyone you want. Dropbox is the thing that threads everything together, so our lives are more connected.

Exploration by Fanny Luor

Fanny Luor explored geometric building scenes where devices were integrated with the scenes. The minimal approach had legs and stood out compared to the louder concepts that were being presented.

Concept Sketches by Dominic Flask

Dominic Flask explored a mix of concepts where files lived inside and outside of the device.

Concept pieces by Danny Jones

Danny Jones explored a whole new approach to illustration by experimenting with 3-D elements. This approach makes a more literal connection to how Dropbox houses all of your stuff, including music, raised-bed gardening plan PDFs, and photos of the bike parts you’re selling on eBay. Danny explains, “We were trying to move the focus towards celebrating the variety and texture in people’s digital things and how Dropbox would be the ideal place for that and really championing that instead of just being this cloud-based hard drive.”

Illustration by Chris Delorenzo

Chris Delorenzo was contracted to explore editorial approaches. It sounds obvious now, but his explorations that didn’t include technology were an important approach to help the team remember that users didn’t care about their phones as much as they did their life adventures.

Concept Illustration by Scott Martin

Scott Martin, aka Burnt Toast, was contracted to use his more surreal style to find new conceptual territories. There were some interesting ideas around how Dropbox adds functionality to devices with these machine-like illustrations.

There were so many good options from some of the best minds in the biz. So how does one decide the best direction? There are many considerations: brand equity, scalability, current trends, business needs, marketing goals. The list goes on and on. Two concepts stood out as speaking to the brand in an evolved way. The unbroken line concept spoke to the team because the aesthetic itself had conceptual weight. The other concept that spoke to the team was the idea of monumental scale. The idea that Dropbox allows devices to safely hold the entirety of your life’s dreams had a lot of potential. And to top that off, the simplicity of Fanny’s work was resonating as an important consideration for the next round of creative. Ultimately, these ideas were selected and Zach and Brandon worked on taking them to the next level.

Final piece: Illustrations by Zach Graham and Brandon Land, animation by Buck

The final direction created an active world where Dropbox seamlessly plugged into anyone’s lifestyle. A skate video could automatically be saved from your phone. A trip to a waterfall was forever saved for you to look back at. The concept related to the nature of the product at the time. Dropbox sat in the background and just worked the way you needed it to.

“As for the concepts, we worked really closely with the writers. We looked to them to drive the copy and then we would concept illustrations from there. We would get the headline, “Take your docs anywhere,” and then we would break down the pieces to start to illustrate a universal story.” –Brandon Land

To put on the finishing touches, the Brand team worked closely with animation studio Buck to bring the illustrations to life. Once the illustrations moved, they brought the concepts to life in a subtle yet engaging way. In my opinion, it was fantastic!

“It was an exciting time for me, because the whole style was changing. The new style felt very wild wild West. We got really loose with the vector and literally drawing with vector.” –Fanny Luor

The Brand team had its first big success. The site design was beautiful; the writing was beautifully simple. Kristen had shown what a Brand team could be. She worked tirelessly in the background to fight for good design, good systems, and bold thinking. As she helped Dropbox through the growing pains, the creatives were able to focus on creating their best work. But as designers, we know we’re only as good as our next gig, so onward to the next challenge we go.

Video shares quickly to any device

“I really had to learn how to collaborate openly with people. Especially external collaborators. For a while, I thought if their work was better than mine then I’d be out of a job. But ultimately we were able to work with them to open up new possibilities in our work.” –Brandon Land

The next interesting challenge: drawing characters

Character illustrations by Buck

Mounting pressure from other parts of the company to show real people using the product was becoming intense, but at this point, it made sense. Dropbox needed to educate people on how the product makes life easier for them. It’s difficult to communicate an easier life without showing a person living that life. The only problem was that every other company was using photography to show real people. For the Brand team, that type of photography looked forced and rarely felt genuine. This was another chance for the team to show a more original way forward. They peeled back the layers on the desire to show people using the product. They boiled it down to its essence, and they came to the conclusion that a character style was needed to meet the company’s education needs. It was time to make a product video unlike any other at the time.

*“The home page proved to be too controversial of a surface for developing this new illustration style. The pressure was too much for a lot of folks on the team. Our real breakthrough with the illustrations came through the collaboration with Buck on a video we were working on, called ‘What is Dropbox?’ Lisa Sanchez, Danny Jones, and I wrote the script for this short piece. We shared the script and wrote a brief for Buck, and this is really where we saw the potential of the new style come to life.” * –Kristen Spilman

If you’ve ever needed to illustrate characters for a company, then you’ve inevitably run into the challenge of drawing people in an inclusive way. It’s imperative for your audience to be able to see themselves in your work. So the Brand studio decided to work with the experts on character creation. They reached out to Buck once again to help concept characters and create our “What is Dropbox?” animation. Buck, brilliant as always, came up with a set of characters. They resembled humans, but they most certainly were not. They transcended races, genders, and body types. In some ways, they were like the Helvetica of characters, universal and ready for every occasion.

Buck’s work on the “What is Dropbox?” animation provided a whole new set of tools for the Illustration team to play with in product and marketing. It was huge because they were able to get a little weird and were able communicate a lot more with their work. The brand became much more relatable, and the burning desires of the team to create more conceptual editorial style work could be satiated.

Dropbox’s current brand: running with the characters of a delightful universe

Illustrations by Brandon Land

After the creation of the new character style, the Illustration team was able to go buck wild creating a magical world of characters experiencing any number of situations. They flew on paper airplanes, carried massive documents, and popped through digital portals to collaborate from alternate universes. In other words, shit got real fun.

On the internal politics front, the brand had cemented the power of illustration. It proved the worth of brand illustration not only to the Dropbox community but to seemingly every other tech company out there. The style progressed and stretched its boundaries. There were the expected pushbacks, and some great ideas fell on the cutting room floor. But that’s par for the course in the creative world, right? Ultimately, the illustration style had cemented its role in the Dropbox identity, and it was used pretty much everywhere, including product, marketing, comms, and advertising. You name it, and illustration brought life and meaning to it. In fact, I’m pretty sure there are no other companies out there that use illustration to the extent Dropbox does. From an illustration nerd’s perspective, it’s pretty damn impressive, and it’s certainly inspiring.

File not found by Zach Graham

Over the last few years, the Illustration team has been stacked with talent, including Zach Graham, Fanny Luor, Brandon Land, and Dominic Flask. While the illustrators all have had their hands in pretty much every aspect of the style, each illustrator had a specific interest or flair to their work. Each strength pushed the whole team to evolve into a more well-rounded illustration machine. The style was forged into its most refined nature, and it burst with delight. Zach continually pushed himself to find more innovative editorial-like concepts. Fanny had a keen ability to infuse emotional connection in her work. Brandon brought life to the characters in aspirational ways. He also brought a more outlandish flair to the work. Dominic was able to filter the wacky style into something a little more palatable for the more conservative Dropbox Business customers. Their talents carved a hard-working and versatile brand path that adapted well in almost every situation.

Illustration for the Dropbox blog by Fanny Luor

So this is the part of the story where I come in. I’m fortunate to have a chance to lead the Illustration team, including Brandon Land, Fanny Luor, and Justin Tran. A great many people have fought hard for Brand to earn its place at the table. And as the company continues to grow by leaps and bounds, I know new challenges will continue to pop up. The unfortunate thing is that none of us have a good map to guide us, because this whole setup is still fairly new for our industry.

The Dropbox Brand studio is in a really good place these days. Illustration is adored as an inextricable characteristic of the brand. In fact, it’s hard for people to believe that there was ever a time when illustration wasn’t mandatory. We’ve come a long way with the illustration style, but now every other company out there uses illustrations in their brand. It’s actually kind of insane. They are all enjoying a new pr0-illustration reality that early Dropbox designers and illustrators had to fight tooth and nail for.

Illustration by Justin Tran

Finally, a highly original list of lessons learned

So, what’s next? Well, I’ve never been one to play it safe. I tend to get bored pretty quickly when things are stagnant. So the process of learning about the countercultural history at Dropbox has been pretty inspiring to me. I’ve already found ways to incorporate lessons learned into the way we approach illustration in the future. And I’m incredibly lucky to be surrounded by a team of bold creatives who are pushing me to take even bigger risks than I might be comfortable with.

So, for now, I leave you with the most original thing ever. A list of lessons learned. Some may call it a listicle. I, too, may call it that. But I’m going to own it and pretend like it’s not cliche. Without further ado: my totally original list of lessons. May it be the last listicle I ever write.

If it isn’t scary, it isn’t worth doing. There are a lot of people out there who like to play it safe. They understand this world we live in is a machine, and it’s convenient to be a cog. Fit in, get paid, settle down, and pretend like death isn’t around the corner. But I think it’s important to add a little of yourself to everything you do. That’s a scary thing to do. It means vulnerability and the chance of being wrong. It means swimming upstream. If you need proof, everyone that fought for the Dropbox brand to be unique is doing just fine in their careers. They’re respected in their fields, and they’re likely to be working on the next thing that everyone will want to follow.

Never listen to someone who tells you to do it like someone else has done before. There’s a difference between learning from the past and just following trends. The past generally teaches you what not to do. It rarely has the answers for what will be successful in the future. If your company is following trends, then you should be aware that your company is not leading their own destiny. They’re following someone else’s and will most likely always be a follower. You’ll never look back at your life and say, “Man, it was so fun riding other people’s coattails.” Take a chance. It will be worth it.

Just because you have an opinion doesn’t mean you’re right. Design is a lot of work. It’s not an easy field to be in. As a creative, it’s your job to research, explore, test, imagine, build, rebuild, and do it all over again. There’s always someone better than you nipping at your heels. As soon as you figure out what works, everything changes. This means you have to constantly be working to improve yourself. Find good collaborators that you can trust and build bigger things together. Your opinion only gives you the right to test it and work toward turning opinions into knowledge.

Style for style’s sake is stupid. Jon Ying proved it isn’t style that people care about. He didn’t draw to impress other illustrators or designers. He wasn’t trying to win awards. The only reason his illustrations worked was because the concept and communication needs matched the work. You must always remind yourself that your audience isn’t other designers. Designers are fickle beasts who love to judge for judgment’s sake. Trying to please them will not end well for you.

Be kind to people. Your reputation is counting on it. In my many years as a designer, I have heard a lot of stories about how people have treated others. I’ve heard both the good stories and the bad. Drama is something we cannot escape as we are crammed into buildings working on things that may or may not be appreciated by those around us. I’m not sure if there is a way to fix these types of personal problems, but what I do know is that people love justice. If you’re unkind to people, then those people will love to shit-talk you. This design world of ours is so small. It affects your future. Trust me — I’ve burned a bridge or two in my life and years later met new people who already had preconceived notions about me. True or not, those moments tend to have a lasting effect on your life. I think Anthony Burrill’s beloved poster said it best: Work Hard & Be Nice to People.

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