I get these questions (or similarly-phrased questions) often enough that I figured it would be helpful to post my responses somewhere. So, uh, here you go.
Q: What changes did you see in the design process at Dropbox from when you started to when you left and how did that impact you as a designer?
A: When I first joined Dropbox, I was the latest in a team of about a dozen designers in a 400-person company. This small size allowed the whole team to critique one another’s work on a weekly basis, and frequently bother someone at their desk. By the time I left Dropbox, the company was almost 2,000 people, and the design team had grown to about 60 people (including product designers, researchers, content strategists, and illustrators). We went through a series of changes to adjust for our growth, but in the design team there were a few notable ones.
Firstly, the design team became several smaller design teams, each focusing on a particular suite of products or function of the business. For instance, there is a team working on just Dropbox Paper, teams working on Business and Enterprise offerings, and growth teams (like the one I was on for a year!) focused on scaling the product and driving adoption of new features. This narrowing of focus had obvious benefits, but it also introduced risk (and often reality) of a more fragmented product design. My last year at the company attempted to directly address this by building design tools and frameworks, and much of this work has been continued after my departure.
Secondly, researchers and content strategists became a vital function of the design process. As I mentioned earlier, as the design team scaled, our work became somewhat fragmented, and this was especially indicative in content and micro-interactions. We started hiring content strategists and researchers to help validate our decisions, discover new opportunities, and design with a consistent linguistic style. A major side effect of the growth of those functions was increased communication and collaboration between design teams and amongst cross-functional teams.
Oh, right, how it impacted me. Focus is good, teamwork is better. And I have a profound respect for content strategists and researchers. They're often the banner(wo)men pushing design efforts forward and grounding product designers' ideas.
Q: What types of projects have contributed most to your growth as a designer (eg. projects at work, side projects) and any recommendations for someone breaking into the field?
A: There are two different kinds of projects I could talk about here; formative projects which shaped my skill set as a designer, and publicity projects which provided some initial momentum for my career.
The publicity projects were my side projects, and they are all small in scope, but over time have provided value for myself and many others. They are all based on small inconveniences that I could address in my own life and work, and as expected, most things that inconvenience oneself also inconvenience others. Fixing those small problems with web apps (onword.co, brills.me) and frameworks (Animate.css) provided a portfolio rich enough and varied enough to pique the interest of the Dropbox design team. The time I spent (and still spend) on my side projects is some of my most valued time—don’t underestimate the value of ‘dumb ideas’ you may have! If it’s small in scope, play around with any idea you have, whether that means a sketch or buying a domain and working on something with a friend.
As for the formative projects, those are the ones that I did at Dropbox and Facebook. At Dropbox, two projects informed a lot of my professional experience; redesigning Dropbox Pro, and a project called Scooter. Redesigning Dropbox Pro was quite lofty in terms of scope. It touched revenue, core product, legal, and international teams, and with that came many negotiations and compromises. Most interesting to me was the work on the revenue side; designing checkout flows, experimenting with content strategists, and watching how much money our changes made (or lost) for the company. On the other hand, there’s Scooter, the design system I worked on at Dropbox. Unlike the Dropbox Pro work, “shipping” or launching the design system was a very long game. Years long, though I left before I could see it start to take off. It was a lot of working with other design teams to make sure our components met their needs, and a lot of being in the trenches with engineers to learn their pain when it came to working with designers. It was extremely satisfying when things would ship, and extremely grueling and interesting when things slowed down. At Facebook, I spent the first 6 months working on an ads product to allow advertisers to A/B test targeting strategies. I had no prior experience with ads, so it was a lot of learning on the job, but I’ve gained a wealth of knowledge about the advertising industry and about how a company like Facebook operates at scale. (Promisingly, a lot of my ideas for design systems at Dropbox seem poised to succeed at a Facebook, a company 10x the size!)
Q: What do Dropbox and Facebook look for when they hire junior designers?
A: To be completely honest, I don’t have a great measure for the skills we look for any more. It’s been years since I interviewed designers. At Dropbox, I was mostly interviewing engineers, and I haven’t interviewed at Facebook yet, so hard criteria for hiring hasn’t been laid out for me. My only constant advice when this question is asked is that companies like Dropbox and Facebook put much more value into the thought process of a designer than their output. Backing up your solutions with well-thought-out intentions and proof of theory is a skill you can’t Google, and by far the most heavily-judged aspect of an aspiring designer. Part of the challenge of answering that question is that Facebook and Dropbox and other successful companies purposefully embrace diversity of thought in their hiring, so design teams are rarely homogenous enough to define the “template” of a good designer. It’s also really hard to learn the things that make or break a hiring decision—passion, curiosity, thoughtfulness, and rigor. I’m sure you possess those skills, and my best advice would be not to hold back on expressing them.