Product Designer at Dropbox


JennyWen (Product Designer at Dropbox)

San Francisco-based product designer. Currently obsessed with: public transit, reading challenges, and photojournalism.

San Francisco, USA • January 22, 2019

What led you into design?

I started making websites as a kid — Neopets store themes, Myspace profiles, and Piczo sites, but I never realized any of this could amount to any sort of paying job. My time in college was kind of all over the place. I started out studying urban planning, but halfway through, I got bored and started over in a systems engineering program. I didn’t too think hard about my career outcomes at this point. I just knew that I liked both visual art and the sciences and that I wanted to be challenged.

Luckily, I went to the University of Waterloo which requires most students to do a series of 6 internships as a degree requirement. Through these internships, I experimented with working as a software engineer but ultimately discovered what a “UX designer” was by working alongside them in tech companies. Once I realized that there was an actual job that aligned with my broad set of interests (art, engineering, business, psychology), all I wanted to do was find ways to be better at it.

From there, I spent the majority of my time outside of engineering school reading to understand design principles and theories, and paired that with actually practicing it—going to hackathons, freelancing for startups, and running a design club at Waterloo.

What does a typical day look like?

I bike to work and usually listen to a podcast on the way. My long-running favourites are Hidden Brain, Death, Sex and Money, and Radiolab. I generally hate waking up early, but love being at the office while it’s quiet, so I try to get in around 8:30–9:00am, grab a coffee and eat breakfast at my desk.

Every day is sort of different, so I check my calendar and make sure I block off at least a few hours to put headphones on and think. I sit next to the engineers on my team, so I usually try and check in with them at some point in the day, understand where they are and whether or not they need design guidance with anything they’re working on.

The Paper design team has design sessions twice a week where we brainstorm and review work together. They’re some of my favourite meetings since we get to bounce ideas off of each other and the team is just a fun and brilliant crew to hang out with in these contexts.

What’s your setup?


Where do you go to get inspired?

I have a strong attachment to places, so I find I’m most inspired when I leave the city for a week or so. Any shake-up in my routine makes me reconsider what’s possible with my time, and being anywhere radically different from where I live reminds me of all the different perspectives people can have on ways to solve a problem.

New York always makes me feel inspired because there are so many different types of people in one place.


I drove across Alaska a few years ago after spending the summer working in New York and the change of pace was entirely refreshing.


Having said that, I also do love taking the time to explore the city I’m living in more deeply—usually through walking and not just zipping from point A to point B. It always makes me more grateful to be where I am and as a result, more motivated and inspired.


What product have you recently seen that made you think this is great design?

Not really a product, but I went to the Austin Public Library recently and I LOVED it. I’m usually not a fan of how contemporary architecture looks, but the best part about the library was how its form invited people to be active with it and to use it.


I also just love books and public spaces in general, so I was excited that we’re still investing in places where people from all walks of life can go to gather and have equal access to the same learning material.

What pieces of work are you most proud of?

One of my first projects at Dropbox was working on allowing Paper users to make templates.


It was really exciting to be able to give people a feature that they’d been asking for and that would make their workflows for creating docs, faster.

What design challenges do you face at your company?

The design team on Paper used to be just a couple of designers who’d work closely together with engineers. Over the past year or so, as the design team and engineering team have grown as a whole, we’ve had to be more intentional to set up time and share designs with engineers on a regular basis, instead of being totally ad-hoc.

We’re always trying to improve on this front, but some things the team has started to do include printing work out to make design visible in our working space, sharing things on Wake, and inviting engineers to design sessions.

What music do you listen to while designing?

Any advice for ambitious designers?

It’s funny because I still often feel like a misguided engineer, trying to convince people (and myself!) that I’m actually a designer. So, this one’s for anyone who’s starting on a self-learning journey to design:

In my first year of college, I learned about a cognitive psychology concept called the Johari window and it completely changed the way I approached learning new things. Basically, for anything you’re trying to learn, you have the things that you know that you don’t know (known unknowns), but then you also have a lot of things that you don’t know (unknown unknowns) since you’re just a novice.

For me and my design journey, this meant understanding the range of skillsets that were important in design before naïvely plunging head first into say, learning another design tool. I did this by asking experienced designers about what they were expected to do in their roles, as well as getting direct feedback from my internship mentors around what they observed my strengths and weaknesses as. Keeping a check on my self-awareness helped me target the areas I wasn’t quite so strong at and made the learning process less overwhelming—I could be focused instead of trying to learn everything all at once.

Anything you want to promote or plug?

I started using Dropbox Paper before I joined Dropbox last year and one thing I never knew about before I saw all the ways people made Paper docs at Dropbox is all the nifty keyboard shortcuts! There’s a little keyboard icon in the bottom right corner, but here are a few of them:

· #, ##, or ### for large, medium, or small headers
· > to create a blockquote
· /date to quickly add today’s date

Also, a big plug for the Dropbox Design blog because it blows my mind on a regular basis that I get to work with and learn from all the super talented people behind the blog. The blog is mostly a way to make sure that everyone else gets a slice of that awesomeness, too.