Talk about yourself! This is the most common failure mode I see: early-stage founders have an idea of what a job description “should” look like, and that is something impersonal and “professional.” But the Chief of Staff role is pretty intimate, and really any role at an early-stage company is going to be pretty intimate. People who are joining the company at the earliest stages are largely joining because of you, the founder. Especially if you don’t have traction yet. So show who you are! Include your name and link to your LinkedIn (or Twitter, personal website, whatever you like to use). You can also include a quick sentence about your background and / or why you started the company.
If you have funding and especially if you have any noteworthy investors, include any specifics that you can! Especially at the early stages, when the company's entire web presence may be a vague landing page, anything that establishes that you're legit and trustworthy and real is good.
I always like it when the founder says something like “background that *could* be a good fit” or something to the effect of “please apply even if you do not meet all the requirements.” It’s good to give candidates an idea of the types of backgrounds that could be a good fit, but the right candidate could come from anywhere. Studies also show that women are less likely than men to apply if they don’t check every single box, so this can help level the playing field / ensure candidate diversity.
Before hiring for this person, write out a list of 5-10 things you would want your Chief of Staff to take on, if you had already hired this person. By the time this person joins the company, those items may no longer be relevant, but I think this is a good exercise to really concretize the role in your mind / think through what skills and type of person you really need.

How to share your Chief of Staff role

Share it with CoS/BizOps-focused newsletters and job boards, including:
- Me. I run alirohdejobs.substack.com: alirohdejobs@gmail.com
- Post a job for free to the Chief of Staff network
- Submit it for free to this form to get it included in the Startup Search newsletter (~8k subscribers), run by Contrary Capital.
- Email the details to Cody Crook, who runs exitup.substack.com: cody@exitup.io
Share it on Twitter, LinkedIn, and Facebook! Try to make the post pop. You can do just 1 tweet, or a Twitter thread, or a tweet with a picture of the a few paragraphs that explain what you’re looking for
Send the posting to your team members, friends, investors, and advisers explaining the type of person you’re looking for, and asking if they know anyone. Also send them the links to your public posts on social media so they can amplify.
Think about what types of backgrounds you’re targeting, and share accordingly. For example:
- If your company is in biotech and you want someone with that background, think through where people like that might congregate, such as Slack communities, alumni groups, newsletter distro lists where you could find those types of people. Ask your friends in the industry
- If you’re interested in MBAs, share it with MBA programs -- either get in touch with their career center (probably takes a bit longer) or send the JD to someone you know in that program (faster)
- If you’re interested in former consultants, send the JD to people you know who work or who have worked at those companies (eg McKinsey, Bain, BCG, Deloitte, etc.)

Some different titles for CoS-like roles

Chief of Staff / Chief of Staff to the [X]
General Manager (GM)
Founding Operations Hire / Founding Operations Team
Employee #[X]
Founding Team Member
Business Analyst
Program Manager
Project Manager
Generalist
Business Operations Lead
Growth Analyst
Operations Partner
Market Lead
Strategic Finance
Strategic Planning
Core Operations Lead
Community Lead
Head of Strategy
GTM Strategy & Operations
Biz Ops Generalist
Deputy Chief of Staff / Junior Chief of Staff
Business Operations Associate
Operations Associate
Operations
Operations Manager
Strategic Planning Associate / Director
Business Operations & Strategy
Director of Operations
VP Operations
COO

Sample questions to ask Chief of Staff candidates

Where do you want to be in 3 years? 5 years? 10 years?
Do you prefer managing teams or being an IC?
What are some of your strengths? What are some of your areas for improvement?
With what types of people do you usually work best?
Why are you interested in being a Chief of Staff?
The Chief of Staff title is pretty vague. What is your conception of what a Chief of Staff role looks like?
Why are you interested in this role specifically? What about this opportunity really caught your eye?
How do you like to work?
When you assess companies and job opportunities, what are the things you care about most? (eg culture, mission, work-life balance, compensation, challenges)
What has been your most difficult job experience so far? What has been one of your most rewarding job experiences so far?

Compensation questions

Compensation differs dramatically by the stage of the company, how much equity the person is getting, and how senior they are
Compensation surveys from the CoS network:

Operations, Management, HR, GROWTH STRATEGIESFrancesca Tabor15 November 2022

So you want to hire a Chief of Staff - The Ultimate Guide to hiring a Chief of Staff

Guide to hiring a Chief of Staff

Reading to better understand the Chief of Staff role

Some JDs I think are good

Sample JD structure

My recommendations for founders

How to share your Chief of Staff role

Some different titles for CoS-like roles

Sample questions to ask Chief of Staff candidates

Compensation questions

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