Hiring a Chief of Staff is a crucial decision for any company. As your right-hand person, this person will have a significant impact on your success. Over time, we've helped dozens of founders hire Chiefs of Staff. Below, I've summarized the key steps involved in finding the right person for the job.
Conceptualizing the role
The Chief of Staff role is much less defined than your average engineer or sales role. As a result, spending time conceptualizing what you're actually looking for is critical. Here are the exercises I recommend founders use to figure out what they really need.
To start conceptualizing the work this person could work on: Imagine you had already hired this person, and this person was joining the company today. Write out a list of 5-10 things you would want them to immediately take on. By the time this person joins the company, many of these items will no longer be relevant, but this will help you figure out the types of work you'd want this person to take on.
To start conceptualizing the type of person you want: Think through people you know and you've read about. If you could hire anyone you know, who would you want to hire for this role? Tim Cook? Your sister? Your manager at your previous company? Now that you have this person in mind, think about what traits or experience they have that would make them so effective.
Maybe they are super organized and get sh*t done, always responding to message and emails promptly and never letting balls drop. Maybe they've worked in finance or consulting, and would be able to redo the model you built for the company with their eyes closed. Maybe they studied computer science and are very comfortable work with engineers. Maybe they have sales experience, and can help you refine your GTM and sales motion.
Writing the job description
When reviewing founders' job descriptions, the most common piece of feedback I give to founders is to talk about yourself. This is actually the case when I'm reviewing any job description, regardless of role, but it's even more critical when drafting a Chief of Staff job description, because this person will work with you so closely.
- 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.
Sharing the role
Share it with CoS/BizOps-focused newsletters and job boards, including:
- Me. I run alirohdejobs.substack.com: alirohdejobs@gmail.com
- Post a job 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.
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.
Determining the right title
Sometimes a Chief of Staff might not be the right fit for your needs. It's always a good idea to take a moment and evaluate your requirements. Perhaps there's another role or solution that would be better suited for your specific situation. Some roles that are closely related to what a Chief of Staff does include:
- Chief of Staff / Deputy Chief of Staff
- General Manager (GM)
- Head of Strategy
- GTM Strategy & Operations
- Business Operations / Business Operations Associate / Business Operations Manager / Business Operations Lead
- Operations / Operations Associate / Operations Manager
- Biz Ops Generalist
- Founding Operations Hire / Founding Operations Team
- Business Analyst
- Program Manager
- Project Manager
- Generalist
- Growth Analyst
- Operations Partner
- Market Lead
- Strategic Finance
- Strategic Planning
- Core Operations Lead
- Community Lead
- Strategic Planning Associate / Director
- Business Operations & Strategy
- Director of Operations / VP of Operations
- COO
Sample interview questions
- 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?
Determining compensation
- 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: 2023, 2022, 2021, 2020, 2019
Sample JD structure
[Company X] is hiring a Chief of Staff to! This is an opportunity to [why the role is cool].
Location:
About [Company X]:
Company X is reinventing…
Already, we’ve… [something about any existing traction]
Our team comes from…
Our investors include…
About [Founder Y]:
The Chief of Staff will work closely with [Person Y]. [Person Y] founded the company in [Year] because she… Her background is in…
Your work could include:
-
Sample skills and backgrounds that could be a good fit:
-
Why you might be excited about this role:
-
Why you might *not* be excited about this role:
-
How to apply:
-
