I've helped dozens of founders hire for Chief of Staff. Here's how to do it.
Clarify what you need
The Chief of Staff role is less cookie cutter than other startup roles. It varies wildly company to company, so it's worth spending time figuring out what you actually need. Two exercises to figure this out:
Imagine this person starts today. List 5-10 things you'd hand them immediately. These will change by the time you actually hire, but this reveals the type of work you need done.
If you could hire anyone you know for this role, who would it be? Tim Cook? Your sister? Your old manager? What specific traits make them right for this?
If the exercises reveal you need a GTM lead or operations manager instead of a generalist Chief of Staff, hire for that specific role.
Check compensation benchmarks
Compensation varies wildly by stage, equity, and seniority. Use the Chief of Staff Network surveys: 2025, 2024, 2023, 2022, 2021, 2020.
Compensation differs dramatically by the stage of the company, how much equity the person is getting, and how senior they are. I highly recommend taking a look at the compensation surveys published by the Chief of Staff Network: 2025, 2024, 2023, 2022, 2021, 2020.
Put some real effort into writing the JD
Include your name and link to your LinkedIn, personal website, or Twitter. Add a sentence on your background or why you started the company. This role is intimate. People join because of you, especially pre-traction.
If you have funding or notable investors, say so. At early stages when your entire web presence might be a vague landing page, anything that establishes legitimacy helps.
Say "backgrounds that could be a good fit" and "apply even if you don't meet all requirements." The right person could come from anywhere, and this improves gender diversity in your pipeline.
Test out actually working together
Do a paid working session before you hire. Give them a real project (4-8 hours, pay them for it) and see how they work. This reveals way more than interviews.
Get input from others
Have finalists talk to people who know how you work - cofounders, close advisors, key investors. We know ourselves, but we don't always know how to work with ourselves or what our blind spots are. Debrief with them after about what they thought, what they noticed, and any potential green or red flags.
Distribute wildly
Share on CoS/BizOps newsletters and job boards.
Post on Twitter, LinkedIn, and any relevant communities you're in.
Send to investors, advisers, team members, and friends. Ask if they know anyone (the best fits often come from your existing network). Send them links to your public posts so they can amplify.
Job description template
[Company] is hiring a Chief of Staff. This is an opportunity to...
About [Company]: We are reinventing... Already, we've... Our team comes from... Our investors include...
About [Founder]: The Chief of Staff will work closely with [Founder]. They started the company because... Previously, they...
Your work could include:
Sample skills and backgrounds that could be a good fit:
Why you might be excited about this role: