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Walnut Hill School for the Arts

Catching Up with Gillian O’Brien ’13

This month we spoke to Gillian O’Brien, a theater major-turned-startup founder and current Chief of Staff for Dover, a recruitment agency. Gillian’s recent job search was detailed in her Medium article, ”How I found an amazing job (during the pandemic).” We chatted with Gillian about her journey from Walnut Hill to the startup world.

What brought you to Walnut Hill originally, and what was your experience like as a theater student here? Do you have any favorite memories from those years?

I went to Walnut Hill to study theater. My experience as a theater major was intense and unique! Actors are some of the most creative, funny, imaginative and open people, and as a result, I had some of the most spontaneous, goofy moments during these years. It was really cool to be in an environment where people wanted to create things all the time, and it felt like entire songs, skits, etc. were being improvised on the spot. I also really valued the exposure not just to learning different acting techniques, but to working in different areas of production. It gave me perspective and appreciation for everything that goes into making a show.

In my senior year, I became really close to the girls in my dorm (Stowe) and we are still friends today! I remember during Halloween that year we decorated our dorms to make them “haunted” and held seances for students with Ouija boards. Our dorm parents participated, too . . . it was amazing.

Catch us up on the years since you graduated—what did you do after Walnut Hill, and how did that lead to the career you have today? 

After graduating from Walnut Hill, I started at NYU Tisch in their acting program. After a semester, I started to feel a little stuck. I found that college acting programs were actually really similar to Walnut Hill (in my experience, at least) and I was restless to push ahead and broaden my horizons. 

I stayed true to my core drive (creating things), but I shifted the way I was funneling my creative energy in the world from art to business. Creating products and services requires a lot of flexibility, adaptability, good listening skills, improv skills, storytelling, and directorial savvy; things I learned from my time as an actor!

I ended up getting my B.S. in Nutrition and minoring in Child and Adolescent Mental Health Development while freelancing as a growth consultant for startups and influencers.

In 2018, you and your sister founded a startup called Cherry. Can you tell us a little bit about this process, and the lessons you learned about starting and running a company?

After graduating from NYU, I was once again restless, this time to enter the “real world” and start working. I ended up bringing my experiences with influencers into a company called Terez, where I worked as Manager of Social Media and Influencer Marketing. 

After a few months, though, my restless feeling hadn't gone away. I realized I was limited by being siloed into one department. I had so many ideas and wanted to be free to execute on them. Not many companies are willing to give a ton of decision-making power to a new grad, so I started thinking of other paths forward.

I've always been really close to my older sister, and she was working as an engineer at the time. Through a series of conversations, we realized we had the right combination of skills between us to start a startup. 

We went through Y Combinator in 2019 (fun fact: Kanye West recently tweeted about YC), raised $700K in total funding, sold into 40+ organizations, and scaled our product to 1,000+ users. We were featured in TechCrunch and Forbes and ran operations for about a year and a half. 

In response to COVID, we unfortunately had to shut down, but the experience was absolutely incredible and opened up so many doors for both of us. From running Cherry, I learned how important it is to advocate for yourself and follow your gut. Only 2% of venture capital goes to female founders, and tech is a male dominated industry—it was easy for me to feel lost and want to seek advice from everyone else. But at the end of the day, the best business decisions I made were the ones that came entirely from my co-founder and me. Learning to trust myself was my biggest lesson. :) 

Tell us about your work with Dover—what excites you most about this new position, and what are you hoping to accomplish? 

I'm now working at a recruiting-tech startup called Dover (also backed by YC). As our Chief of Staff, I act as an extension of the CEO, taking on everything from sales to hiring to culture to customer ops to product—whatever needs to get done that day. I love working cross functionally and having a high-level understanding of the business. It’s a perfect role for me because I have the freedom to do so many things. I’m hoping to learn as much as I can about what it takes to make a business successful and help Dover reach its full potential. On the side, I like to write career and industry blogs and speak on panels/for workshops (especially to high school and college student audiences!). In this way, I still get to use the performance skills I learned from Walnut Hill.

Do you have any advice or words of wisdom for our most recent alums, the Class of 2020, who are just entering their post-Walnut Hill journey?

Yes! One of the harder things for me to do after graduating from Walnut Hill was to step away from pursuing theatre as my main career path. But my experiences in the arts are interwoven into so much of what I do today, and will always continue to be. I’ve found ways to make art part of my daily life for fun, fulfillment, and expression. I also use what I’ve learned from the arts to serve my professional life.  

I would encourage the Class of 2020 to follow their intuition and pursue lots of different experiences in college and beyond. The next 5–7 years after graduating is a time to really solidify who you are and learn about yourself so that you can forge a path that will bring you joy. :)

Don’t be afraid to explore, try things and fail, pick something up then put it down . . . and don’t freak out if your path doesn’t look like you thought it would. At 18, I never would have imagined that I would be doing anything but theatre—but I’m really happy with how things ended up. 

Also, keep in touch with your friends from the Hill. It’s such a unique place and you’ll feel so grateful to have people to laugh with about the memories that only you all would possibly understand!

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