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Posted 14 December 2020
Introduction by Siham Ali

Dropbox Design product designer, Chelsi Alise Cocking, on how setbacks can be fulfilling

Product designer Chelsi Alise Cocking’s journey to Dropbox Design was not an altogether smooth one. After being recommended for a product design role by her mentor and friend, the job offer initially fell through. But, unexpectedly, the opportunity came back around under a year later. Fast-forward to 2020 and Chelsi is constantly thinking about the present and the future. As part of the Previews team, Chelsi works to help users to view, preview, and better interact with their content and files. Here, we talk to her about how setbacks can actually help propel your career.


Chelsi Alise Cocking

Job Title

Product Designer, Dropbox (2020–present)

Previous Employment

UX Designer, Procore (2019–2020)
Product Designer, Honest Buildings (2018–2019)
User Experience Design Intern, Apple (2017)
Summer Technology Analyst, Goldman Sachs (2015–2016)


B.S. Computational Media, Georgia Institute of Technology (2013–2017)
Minor in Computing & Business, Denning Technology & Management Program (2015–2017)

Social Media


What I do

How would you describe what you do at Dropbox Design?
I’m a product designer for the Previews team at Dropbox. The Preview is essentially the place in Dropbox where our users can view (preview... ) and interact with their content and files.

As the product designer for this team, I’m responsible for executing and delivering the designs. I’ll either be working on new features or making iterations on pre-existing ones. I work both in the context of the present, asking: What features are we designing and implementing on the Preview now? And what do we want to do with Preview in the future?

I work with my engineers and product manager counterpart to implement these features and understand how they impact and serve our users. In a nutshell I spend most of my time designing in Figma, writing in paper docs, and sitting on Zoom meetings!

“[Dropbox Design] has a culture of humanity, care, and understanding. Making sure your teammates are okay is a priority.”

If you could pick one meme to describe what it’s like to work at Dropbox Design, what would it be and why?
I picked this @dinosandcomics meme (below) because the culture at Dropbox and within the Dropbox Design team is very caring. For me this has been very refreshing, especially during these difficult times.

While Dropbox Design has a culture of accountability, ownership, high quality design, and making sure you get your s*** done, it also has a culture of humanity, care, and understanding. Making sure your teammates are okay first, for example, is a priority.

How did you land the job?
At the beginning of summer 2019 I was looking for a new place to continue growing as a designer. I reached out to my friend and mentor in design Rebecca Hillegass. She recommended me for a role at Dropbox and referred me to Jenna Bilotta, who was the Design Director at Dropbox NYC (and is, by the way, an amazing person). She’s a design leader who instills belief in you through her mentorship, and I needed to regain some belief in myself as a designer at the time.

In May of that year I went through the interview process for the role. I had a phone screening, then a portfolio presentation, followed by a full day of on-site interviews, the whole shebang… Finally I was offered the job! However, the opportunity for employment fell through due to headcount and reorganisation. So I was basically back to square one.

“Even though things didn’t temporarily work out, the mentorship and interest in my design career never faded.”

What I valued about this experience most was even though things didn’t temporarily work out, the mentorship and interest in my design career never faded. Dropbox Design as a whole kept me in the loop with their design community.

Through design events at the NYC office, and Ladies Who Create dinners, for example. I met some great companies, including some Dropbox Design members who also became mentors to me, like Roxy Aliaga and Wes O’Haire. That experience of being embraced by the community was very valuable to me during that weird job searching period.

Jenna stayed in contact with me and in December 2019, she reached out and notified me that they got back headcount for a product design position in NYC. She asked if I was still interested, and I happily went into the offer stages and accepted. I joined Dropbox the next year in February 2020. It was a long, unique, full-circle process, but in hindsight, a fulfilling one.

Abstract UI versions of Dropbox Preview

What recent project at Dropbox Design are you most proud of?
I’m most recently proud of the responsibility I’ve been given to take ownership as the product designer over the Preview at Dropbox. The Preview is a key surface in Dropbox that has been worked on for many years, by many people before me. So to have the responsibility of leading design for that surface has been a new challenge for me this year that I’m very excited about and happy to be taking on. I feel like I'm experiencing a new challenge and growth for myself as a designer.

I’m also really proud whenever I can get involved in the Dropbox Design community. It’s a great and vibrant space that reaches the design community in technology at large. Contributing to that in any little way I can makes me happy. We have things like Diverse Dropbox Design (3D), Ladies Who Create, and working with the Inneract Project – most recently I’ve worked with Paolo Ertreo and team to participate in teaching design workshops to kids through the Inneract Project, which empowers underrepresented youth through design education, and links them to opportunities to explore design in their careers and lives.

What’s your favourite thing on your desk right now?
Desk? What desk? I don’t really have a set desk right now. I roam around at home, which I actually don’t mind doing.

Abstract UI versions of Dropbox Preview

How I got here

Did you complete a degree, and has this been helpful to your work?
I studied computational media at Georgia Tech. For context, computational media is an interdisciplinary degree that combines computer science, digital media, and design. It 100% helped me in the work that I do now, because my degree introduced me to user experience design and the idea of human centred design.

Prior to studying, I didn’t even know this was a field that existed. I’m very thankful for being exposed to that because I discovered something I truly love doing.

“Whether you’re self-taught or ‘formally’​ trained, you need to want to put in the work.”

Do I feel that product design requires formal training? No. Do I think going to college for product design or a related discipline is one of the ways to get there? Yes. I found that route to be extremely helpful for me. But regardless of college as formal training, I think what you really need is the drive to want to learn and study product design. Whether you’re self-taught or ‘formally’ trained, you need to want to put in the work.

One of the things that I’ve noticed since my first UX internship role is that everyone seems to have entered in a different way. Someone I met in UX came from an electrical engineering background, while another came from a music background after studying classical piano in college.

Chelsi on Zoom

My advice

What advice would you give an emerging creative wanting to do the same kind of work?
Go after it. That might sound a bit lofty but if you have a passion, don’t get stuck in overthinking how to get there, and just find a way to dive in and get started. Start doing it. Start practicing it. Whether thats through side projects, bootcamps, or even a full-on degree. Reach out to others who are doing it.

If you could share one image, recommend one website, Instagram account or similar – what would it be and why?
I think we can all agree that there’s a lot going on in the world right now. One thing I’ve been trying to do more of is find things that bring joy into my space. So one thing I’ve been turning to is comedy. I recommend the Stand Up comedy section on Netflix. Have a laugh. Laughter is fantastic.

I’ve also turned to things that give me the news, but in comedic doses – I don’t know about your personal experience, but I’ve been bombarded by not so good news constantly this year. So I go for things like The Daily Show with Trevor Noah or The Late Show with Stephen Colbert.


Dropbox Design is a Lecture in Progress company partner. Every year, Lecture in Progress partners with like-minded brands and agencies to support our initiative and keep Lecture in Progress a free resource for students and emerging creatives. To find out more about how you can work with us, email [email protected]

This interview is part of a series of articles profiling Dropbox Design. See the In the Studio With interview here.

Introduction by Siham Ali
Mention Dropbox Design
Mention Chelsi Cocking