Looking for a new Chief of Staff role?
(this is from my Substack post published November 16th 2025)
In today’s competitive Chief of Staff job market, “standing out” as a candidate is really important to potentially get a CoS role.
Here are some things you could do to improve your chances:
start working with a CEO on a project and then potentially expand from there. I have had success with this in the past.
pitch a CoS role when the company is a hiring for an EA role. Make sure this role is eventually scoped as a CoS role, not an EA role though. This approach likely makes more sense at a really small company.
talk to a current CoS about their role and see if they might be looking to leave their role soon. It is said that the CoS role usually lasts around 18 months, so this leads to increased role turnover velocity creating new opportunities.
attend an event a CoS is speaking at, like this one, to learn more about them and potential ways you could help them
ask a CoS if another CEO has reached out to them to learn more about the CoS role in general. I have heard of CEOs doing this, so this could be another way of learning about a role before it’s officially posted online.
do an audit for a CEO on a certain aspect of their core business that you know well. I did some community-led growth audits a few months ago and I got at least one client from doing this! I posted on LinkedIn that I was doing a few audits and it worked for me!
help a CEO with the core things that are typically important to a company like business development, hiring, etc. Do the job before you have the job :)
pitch and get a fractional or part-time CoS role, and then aim to expand your scope from there!
Speaking of attending an event that a CEO is speaking at…
I am hosting a Podcast Mixer with Ashwini Anburajan, the CEO of Obi, who is hiring a Chief of Staff in New York.
When: this Wednesday November 19th at 6:30 in Union Square
Apply to join us this Wednesday here!