Gillian O'Brien

Published in Chief of Staff Network

·Mar 1, 2022

Who, What, When, Where: How to hire a Chief of Staff

After having spent a year and a half in the Chief of Staff role, one of the most common requests I get is to help people with CoS hiring. I’ve written from the candidate perspective about my own experience as CoS, and about the experiences of 14 other CoS. In…

Chief Of Staff

6 min read

Chief Of Staff

6 min read

Published in Chief of Staff Network

·Aug 10, 2021

My first year as Chief of Staff at Dover: 7–40 employees, 3–23M in funding, 60–150+ customers

Last year I wrote about about my job search as an ex-Founder & why I chose to work at Dover as Chief of Staff. Later, through 13 interviewers with other Chiefs of Staff, I learned how compelling yet mysterious the role was to many. Now, one year later, I’m sharing…

Founders

9 min read

My first year as Chief of Staff at Dover: 7–40 employees, 3–23M in funding, 60–150+ customers

Founders

9 min read

Published in Chief of Staff Network

·Dec 8, 2020

I interviewed Chiefs of Staff from Google, Lyft, Twilio, Uber, Chime & more. Here’s what I learned.

I shut down my company in response to COVID & have been documenting my work experiences since — including my journey to determine my post-founder career. I ended up taking a Chief of Staff role at Dover & wrote about that decision here. Since starting, I’ve gotten tons of questions…

Startup

13 min read

I interviewed Chiefs of Staff from Google, Lyft, Twilio, Uber, Chime & more. Here’s what I learned.

Startup

13 min read

Published in doverhq

·Sep 1, 2020

How I found an amazing job (during the pandemic)

Last month I wrote a story about my job search as an ex-Founder, & said I’d write a “Part 2” about selecting a job & where I ultimately ended up. I’m excited to share that I’ve started a new journey at Dover as Chief of Staff. In this article, I’ll…

Coronavirus

13 min read

How I found an amazing job (during the pandemic)

Coronavirus

13 min read

Jul 20, 2020

Figuring out what’s next after shutting down your company

Our last story about shutting down Cherry / fundraising during Covid got a ton of great feedback. Now, I’m sharing a follow up piece about figuring out what to do after your company has shut down. I am a non-technical person and this piece will reflect that perspective My co-founder…

Startup

10 min read

Figuring out what’s next after shutting down your company

Startup

10 min read

May 4, 2020

Cherry is Shutting Down + Our Story

After 17 months of helping workplaces become more personalized, we’ve made the difficult decision to shut Cherry down. While Cherry helped spearhead a new way to provide modern benefits to employees, a confluence of factors have hindered our ability to raise funding. …

Founders

2 min read

Founders

2 min read

Published in Female Founders Lead the Way: Startups, Pitching, Marketing, Building, Investing

·May 4, 2020

🦠 Fundraising During COVID

In October 2018 my Co-Founder Emily & I came up with the idea for Cherry. We moved to San Francisco to go through Y Combinator in early 2019 and raised a $700k+ angel round which we used to build & launch our V1. Our product solved the engagement problem with…

Covid 19

6 min read

Covid 19

6 min read

May 4, 2020

💰 How Not To Fundraise

Fundraising

4 min read

Fundraising

4 min read

May 4, 2020

💡 How It Started

Startup

5 min read

Startup

5 min read

Dec 17, 2019

What it’s like to start a company with your sister

So, what’s it like to work with your sister? Of all the questions I’ve gotten this year about Cherry, this is possibly the one I’ve heard the most. Sibling relationships come in all different varieties, so I understand why people are surprised when they learn that my co-founder is…

Startup

5 min read

What it’s like to start a company with your sister

Startup

5 min read