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What It’s Like To Be A Chief Of Staff

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The Chief of Staff role is becoming more and more a mainstay in technology startups (in fact, dYdX and LaunchDarkly are hiring CoS now). However, it is frequently one of the most mysterious jobs that simply call for a candidate to be a super-connector and a “jack of all trades.”

Prior to becoming a Chief of Staff at Check myself, I hardly knew what the role entailed. But after growing restless working as an investment analyst at Goldman Sachs, I discovered Check and sent an email to see if Check was hiring any generalist roles. Though they hadn’t posted an official job post, they suggested that I’d be a good candidate for a Chief of Staff role.

The blessing (and the curse) of a Chief of Staff job is that it is an amorphous and constantly evolving job. Now that I’ve spent over one year at Check, I’d like to demystify the job a bit and help others figure out if becoming a Chief of Staff is the right route for them.




Why Would You Want to Be a Chief of Staff?

For me, I was looking for the opportunity to serve as a sort of “apprentice” to a founder that I respected. When I saw Check come out of stealth and announce its Series B, I really liked the product and mission. The founder, Andrew Brown, seemed like the perfect person from which to learn.

The Chief of Staff role provides a unique opportunity to view and understand a company from the vantage point of a CEO. From that vantage point, you can gain a ton of learnings and perspectives that are nearly impossible to grasp from more niche positions like product manager or engineer.

At the same time, it does give you the ability to experience many different functions at the company across product, sales, operations and more. This role is perfect for someone that wants to learn how to plan and execute big-picture strategies, while still understanding the minutiae of different areas of the business.

Key Responsibilities

In this role you'll typically be assigned to one executive, usually the CEO (though at larger companies you might support a CMO, CPO, etc). As a Chief of Staff joining a Series B-stage company, I found that my daily tasks tended to fall into three main buckets. This is a bit of what you can expect once you’ve stepped into a similar role.

  1. Direct support to the CEO: This included small things like calendar management, as well as larger things like serving as a sounding board for the CEO when thinking through company strategy. Whether it was writing a first draft or interfacing with other stakeholders, I worked as the CEO’s right-hand man.
  2. Managing internal workstreams and processes: These tasks were more about making sure processes across the company ran smoothly. This included preparing agendas, drafting the key topics for the weekly company all-hands, taking note of action items from important meetings, supporting board meeting prep work, writing the first draft of monthly investor updates, ensuring planning cycles go smoothly, etc. Overall, I was constantly thinking about where existing processes could be improved.
  3. Pushing forward special projects across the company: This involves serving as a “Swiss army knife” where the CEO can slot you into any area of the business. You frequently jump into special initiatives that could use a helping hand and then work to solve those business problems. This bucket took up the majority of my time. Some examples of this include acting as a recruiter, helping to stand up our risk & fraud organization, aiding with sales enablement, and taking the pen on key pieces of marketing.

Important Skills to be Successful

As with many startup jobs, the ability to navigate ambiguity is a strong differentiator between a good and bad Chief of Staff. Demonstrating that you have the ability to work through unstructured problems and drive towards outcomes is important.

In this role, it is critical to stay nimble (and curious) as you wear different hats and help the company stay on track. You need to be someone that is proven to be proactive. Communication is also a key skill.

How to Land a Chief of Staff Role

If the activities above sound interesting to you, Ali Rohde has a weekly newsletter that highlights interesting open Chief of Staff jobs on a weekly basis, as does Startup Search. This is where you can easily browse through a ton of open roles and apply to the ones you’re interested in.

When assessing whether a role is a good fit for you, one of the most important things to do is index heavily on the executive that you will be supporting as their Chief of Staff. It goes without saying that this will be your most important relationship, so you really want to make sure to spend some time with that person and get a feel for who they are and what they are looking for in a Chief of Staff.

Being a Chief of Staff is an incredible opportunity to get a broad view of how a seasoned CEO thinks about operating a startup. It’s a great way to rapidly ramp up your level of thinking, and that can open up many doors both internally and externally as you progress along your professional journey.