When we left the story, 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

Concept exploration by Zach Graham

Sketches 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.

Concepts sketch by Brandon Land

Concepts sketch 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

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

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.

Connectivity concept sketch by Zach Graham

Connective thread concept exploration by Brandon Land

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.

Animation by Buck

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.

Illustrations by Brandon Land

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.

Concept sketches by Fanny Luor

Illustration from a sticker set by Fanny Luor

Illustration by Dominic Flask

Illustrations by Zach Graham

Carrier pigeon sketch by Brandon Land

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.

Illustration by Justin Tran about overcoming writer’s block for the Dropbox design blog.

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 Brandon Land

Illustration about delegating tasks for the Dropbox blog by Brandon Land

Illustration by Justin Tran

Illustration by Fanny Luor

Finally, a highly original numbered 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.