Dropbox Design
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Dropbox Design

Illustrating a more human brand (part 2)

The history of Dropbox brand illustration

Illustration by Brandon Land

“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.

“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.

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.

Concept exploration by Zach Graham
Concept exploration by Zach Graham
Sketches by Zach Graham
Concepts sketch by Brandon Land
Concepts sketch by Brandon Land
Exploration by Fanny Luor
Concept Sketches by Dominic Flask
Concept Sketches by Dominic Flask
Concept pieces by Danny Jones
Illustration by Chris Delorenzo
Concept Illustration by Scott Martin
Concept Illustration by Scott Martin
Connectivity concept sketch by Zach Graham
Connective thread concept exploration by Brandon Land
Final piece: Illustrations by Zach Graham and Brandon Land, animation by Buck

“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

“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

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

Illustrations by Brandon Land
Illustrations by Brandon Land
File not found by Zach Graham
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
Illustration by Justin Tran about overcoming writer’s block for the Dropbox design blog.
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.

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.



We believe joy is the engine that powers the best ideas. We’re designing a more enlightened of working, so you can love the way you work. More on dropbox.design.

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