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Gillian O'Brien
Gillian O'Brien

229 Followers

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Published in

Entrepreneur's Handbook

·Jul 13

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 startups. The advice centers around pitching, selling, and valuing your company while managing a timely process. But what happens when the fundraising frenzy ends? Amidst the never-ending tips for securing cash…

Startup

18 min read

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

18 min read


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

Who, What, When, Where: How to hire a Chief of Staff
Who, What, When, Where: How to hire a Chief of Staff
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
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.
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)
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
Figuring out what’s next after shutting down your company
Startup

10 min read


May 4, 2020

Cherry is Shutting Down + Our Story

After 18 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

Cherry is Shutting Down + Our Story
Cherry is Shutting Down + Our Story
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 and I came up with the idea for Cherry. We moved to San Francisco to go through Y Combinator’s W19 batch. Shortly after, we raised a $700k+ angel round we used to build and launch Cherry V1. Our product solved the engagement problem with…

Covid-19

6 min read

🦠 Fundraising During COVID
🦠 Fundraising During COVID
Covid-19

6 min read


May 4, 2020

💰 How Not To Fundraise

In October 2018 my co-founder Emily and I came up with the idea for Cherry. We moved to San Francisco to go through Y Combinator’s W19 batch. Shortly after, we raised a $700k+ angel round we used to build and launch Cherry V1. Our product solved the engagement problem with…

Fundraising

4 min read

💰 How Not To Fundraise
💰 How Not To Fundraise
Fundraising

4 min read


May 4, 2020

💡 How It Started

In October 2018 my co-founder Emily and I came up with the idea for Cherry. We moved to San Francisco to go through Y Combinator’s W19 batch. Shortly after, we raised a $700k+ angel round we used to build and launch Cherry V1. Our product solved the engagement problem with…

Startup

5 min read

💡 How It Started
💡 How It Started
Startup

5 min read

Gillian O'Brien

Gillian O'Brien

229 Followers

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

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