Gillian O'Brien – Medium

Gillian O'Brien

Gillian O'Brien
in
Entrepreneurship Handbook

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…

18 min readJul 13, 2023

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

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Gillian O'Brien
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Chief of Staff Network

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.

6 min readMar 1, 2022

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

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Gillian O'Brien
in
Chief of Staff Network

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.

9 min readAug 10, 2021

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

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Gillian O'Brien
in
Chief of Staff Network

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…

13 min readDec 8, 2020

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

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Gillian O'Brien
in
doverhq

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.

13 min readSep 1, 2020

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How I found an amazing job (during the pandemic)

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Gillian O'Brien

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.

10 min readJul 20, 2020

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Figuring out what’s next after shutting down your company

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Gillian O'Brien

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…

2 min readMay 4, 2020

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Cherry is Shutting Down + Our Story

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Gillian O'Brien
in
Female Founders Lead the Way: Startups, Pitching, Marketing, Building, Investing

🦠 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…

6 min readMay 4, 2020

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🦠 Fundraising During COVID

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Gillian O'Brien

💰 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…

4 min readMay 4, 2020

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💰 How Not To Fundraise

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Gillian O'Brien

💡 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…

5 min readMay 4, 2020

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💡 How It Started

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Gillian O'Brien

Gillian O'Brien

Accelerator Partnerships @ Pilot.com + Venture Partner @ OCVC | YC alum | former Chief of Staff | NYU grad | gillianroseobrien.com

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