Employee Spotlight #6: Gillian O'Brien, Founder-in-Residence at Pilot

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Check out my latest F2F stories:?

• Startup Spotlight #184: OfficeTogether - OfficeTogether is a workplace collaboration platform purpose-built for the hybrid office. We empower teams to bring their people back together at the office.
• Case Study: Debbie's Users Are More Than Just Customers, But "Key Players" In The Early Stages Of The Startup

Gillian is currently Founder-in-Residence at?Pilot.com?— bookkeeping, tax, and CFO services for startups. Before Pilot, Gillian started a company, Cherry, that went through YC in 2019. She was also employee #5/Chief of Staff at Dover, another YC company, and is a Program Partner for On Deck's CoS academy.?

Pilot's Founder-in-Residence Gillian O'Brien.

Frederick Daso: What was your journey to becoming a Founder-in-Residence (FIR) at Pilot?

Gillian O'Brien: At the end of 2018, I started a company with my sister. We went through the YC W19 batch and ran operations for over 1.5yrs. Though our product and customer base were growing, we couldn't outlast the pandemic. After shutting down operations, I knew I wasn't done being a founder but felt I had a lot to learn before trying it again. I made it my goal to join a seed-stage startup with a lot of potential and see how scaling works from the inside. I became the 5th hire/Chief of Staff at Dover and accomplished my goal. In the year and a half I was there, I helped the company scale from 5 to 65 employees and 6X revenue. I built the 'operator' muscle.?

At the start of 2022, the opportunity to join Pilot as a Founder in Residence came about, and I was excited by the prospect of building the 'networks' muscle more and reconnecting to the founder community.?

Daso: What's the toughest project (professionally or personally) that you worked on as an FIR or in general? What were the most important lessons you learned from that project?

O'Brien: The toughest project I've worked on in my career, hands down, was building Cherry. Between my co-founder and I, we were just one engineer and one person on sales and fundraising. It was a crash course in the basics — how?not?to do sales, how?not?to fundraise. In my eagerness to do everything right, I realized I was book smart and street dumb. At the end of Cherry, I learned an important lesson about distinguishing between signal and noise, building trust with stakeholders, and building something that people?need,?not just something people want/thinks is cool. I wrote a long series of reflections on these lessons on?Medium.

Daso: Who are some of the most inspirational people you've gotten to work with during your career in tech, and why?

O'Brien: Someone who comes to mind for me is Mathilde Collin, who was an investor in Cherry, and whose story I resonate with. Mathilde is a busy CEO, but she still made time to help my co-founder and me do pitch practice. She's also made a lot of her thoughts on leadership and building startups public via blogs. I appreciate that, and it's inspired me to document/publicize my thoughts, too. I look at her career and leadership style as what I'd want to emulate.

Daso: How would you define your company's culture, and how does it create an environment where you can do your best work?

O'Brien:?I like this post from our CEO.?This is the kind of environment I personally need to be successful — one where I have the creative space to experiment and one where I can maintain control of the process of getting to any particular goal. Cultures that are more management-heavy or ask employees to operate more neatly inside the lines wouldn't work for me.

Daso: What's one interesting thing (non-work related) that more people should know about you?

O'Brien: I went to a high school for the arts, where I 'majored' in theatre. My favorite ever holiday is Halloween, and I take it ~very~ seriously. I've been playing Animal Crossing since the GameCube and used the themes from Kingdom Hearts to teach myself how to (badly) play piano :)

Daso: Name three other individuals in the tech industry I should interview!

O'Brien: Here are my recommendations!

• Clara Ma,?Program Director, On Deck Chief of Staff Fellowship
• Richard Wu,?Product at Woflow
• Jessica Cohen, VC @ Partech | Tekton Ventures

Are you a founder looking to learn from other founders on how to build your startup? Are you someone interested in joining a startup as an early-stage employee? Subscribe?to my mailing list, Founder to Founder (F2F):?f2f.substack.com.?

• Startup Spotlights are a high-level overview of a company that comes out once a week every Monday for free subscribers.
• Case Studies are in-depth research profiles on startups published bi-weekly on Mondays for paid subscribers. Paid subscribers also get the Startup Spotlight content included as well. A paid subscription is?7$/month or $60/year. Highly recommended if you're looking to join an early-stage startup that you want more information on.

Check out my latest F2F stories:?

• Startup Spotlight #184: OfficeTogether - OfficeTogether is a workplace collaboration platform purpose-built for the hybrid office. We empower teams to bring their people back together at the office.
• Case Study: Debbie's Users Are More Than Just Customers, But "Key Players" In The Early Stages Of The Startup