So, You Want To Be a Chief of Staff?

The Chief of Staff role feels like the hottest job in startups right now. As a Director of Talent who runs a Chief of Staff Mastermind Network with over 270+ members and has helped dozens of them land their next gig, I’ve learned a lot about the role itself. I’ve been asked a lot about what the role entails, how to land the right fit, and what career paths it can unlock.

To get various perspectives, I sat down with three former Chiefs of Staff—Caroline Vernick, Jason Shuman, Maxine Litre—and Primary’s very own Chief of Staff Francisca Maier, who had previously had that same role at Thinx. I will break down what the role is, how to evaluate fit, and how to leverage the role in your career.

What is the Chief of Staff role?

I asked the panel if there are some alternate titles for Chief of Staff based on their experience and received some illustrative examples: Maxine’s answers were, “Head of Leverage, Information Grand Central Station, Repository for misfit projects, and Executive Shrink.”   Francisca calls it, “Chief of wearing many colorful hats of all shapes and sizes.”

The goal is as simple as it is challenging. The executive team is the CoS’s customer, and it is the CoS's job to make the team successful, Maxine says. Each CoS is different because that leverage comes from a complementary skillset to the CEO to fill the gaps. For example, if the CEO has a technical background, they typically would benefit from hiring a Chief of Staff with a revenue-focused mindset to help build or oversee the go-to-market side of the business.

The role at times may feel like it has the high stakes of a CEO without the upside, but the reward as Jason sees it is the access to the founder, the executive team, and all parts of the organization, including the investors and CEO’s network. (Jason’s network certainly speaks to that point.)

For Caroline, the career accelerator was the relationship she built with her CEO which catapulted her to run Product Operations at Frame.io before it was acquired by Adobe.

Primary’s Chief of Staff Francisca describes the CoS role as the ability to fly really high and understand a business at a ten-thousand-foot view as well as dive deep into specific challenges and problem solve at a tactical level.

The upside is the access and, as Caroline describes, a crash-course in operating at a startup, from goal setting to running projects ranging from Infrastructure to People Ops across the business. The role can be the best way to build a strong operational playbook and work with all the leaders across the business.

What makes someone a good fit for the role? What career paths can the role unlock?

When I am hiring for a CoS, no matter what the level or complementary skills needed, there is one common thread; They are ambitious, high achievers, learning machines, and oftentimes, don’t really know what they want to do. I’ve learned this about a lot of high-achievers: When you can be successful at a lot of things, it’s hard to pick a lane (or function).

Other important and notable traits came up when discussing what personality type and soft traits that make a great CoS. The most critical theme to highlight is comfort with ambiguity and the ability to provide structure and strategy to vague and often undefined problems. This requires a high degree of adaptability and a certain degree of excitement to dive into chaos.

Francisca notes that a CoS is someone with an entrepreneurial mindset who identifies as a generalist and has a passion for ownership. From my own pattern recognition, there are two things I know have to be true for the COS to be successful (and sane): They need to know how to set boundaries and push back, and they need to have a keen sense of prioritization and knowing what will move the needle.

There are three different motivators I’ve seen come into the role:

1. The scrappy generalist who wants to gain a 360 view of the business and catapult themselves into owning a function after their tour of duty (Maxine & Caroline).

2. The entrepreneur who wants to ride shotgun with a CEO before starting their own thing and/or jumping into VC (Jason).

3. The functional operator who wants to expand their scope horizontally (Francisca).

There is inevitably a ton of nuance in this role, but we’ve boiled down three critical pieces to assess a CoS’s opportunity as a candidate:

1. The CEO’s self awareness. Maxine and Caroline called this out as crucial for trust to be built.

2. Clarity on why the company actually needs a CoS and whether that aligns with one’s skills and interests for growth. Jason also notes to ensure that the leadership team is bought in on this as well.

3. The chemistry with the CEO.

Maxine shared some great questions to be clear on before exploring CoS opportunities:

• What part of a business do I have the most interest in getting an immersive experience in?
• What type of company would enable that?
• How could I leverage this extraordinary exposure to become incredible at a job I want?

In short, the most successful “tours of duty” in the CoS role are about alignment and trust. It’s about finding the role and CEO that will have your back, open doors, push you outside of your comfort zone, root for you, listen and receive and grow from your feedback, and ultimately maximize your impact on the business and in return maximize your growth potential.

Do you want to learn more about the CoS role? Apply here to join a network of 270+ members who are benefitting from our programming of professional development, tactical workshops, and learning from peers, both current and former Chiefs of Staff.