Gillian O'Brien – Medium

Gillian O'Brien

Published in

So, You Raised a Series A — Now What? I Interviewed 8+ Founders to Find Out

There’s no shortage of content out there targeted at founders who are in the process of fundraising for their startup. The advice is all…

Jul 13, 2023

So, You Raised a Series A — Now What? I Interviewed 8+ Founders to Find Out

Jul 13, 2023

Published in

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

One of the most common requests I get is to help people with CoS hiring. Here’s how to get it right.

Mar 1, 2022

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

Mar 1, 2022

Published in

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

What a CoS does at a seed/Series A startup, and how my role evolved over time.

Aug 10, 2021

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

Aug 10, 2021

Published in

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…

Dec 8, 2020

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

Dec 8, 2020

Published in

How I found an amazing job (during the pandemic)

Sharing a framework I came up with (The 5 Ps and 6 Bs) for evaluating jobs.

Sep 1, 2020

How I found an amazing job (during the pandemic)

Sep 1, 2020

Figuring out what’s next after shutting down your company

The 4 stages of conversations I had, using my network to ultimately understand what I wanted to do next with my career.

Jul 20, 2020

Figuring out what’s next after shutting down your company

Jul 20, 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…

May 4, 2020

Cherry is Shutting Down + Our Story

May 4, 2020

Published in

🦠 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…

May 4, 2020

🦠 Fundraising During COVID

May 4, 2020

💰 How Not To Fundraise

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…

May 4, 2020

💰 How Not To Fundraise

May 4, 2020

💡 How It Started

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…

May 4, 2020

💡 How It Started

May 4, 2020

Gillian O'Brien

Gillian O'Brien

General Manager @ Remote + Venture Partner @ CRV | YC alum | former Chief of Staff | NYU grad | gillianroseobrien.com

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