What to Consider if You Want to Be a Chief of Staff at a Tech Company

The Chief of Staff role has moved from the halls of Congress to tech startups

When you think of someone with the job title of Chief of Staff, I imagine the first people who come to mind are Rahm Emmanuel, John Kelly or Leo McGarry from the West Wing. The image of a Chief of Staff is someone walking around the halls of the White House or the U.S. Capitol, not someone working in an open office space with exposed brick, visible ductwork and lofted ceilings.

But these days the Chief of Staff title is no longer exclusive to politics and government. Chiefs of Staff can now be found at hundreds of tech companies across the country. I am a co-founder of the Chief of Staff Tech Network, which brings dozens of New York City’s tech chiefs together each month to discuss the do’s, don’ts, and best practices of the position. And we are not alone; there is a similar group out in the Bay Area as well.

So what does a Chief of Staff at a tech company do exactly? Well, it varies widely. It can range in responsibility from a role focused on special projects to something more akin to a Head of Strategy or even a Chief Operating Officer. For more insight into what a Chief of Staff does, check out Scott Amenta’s insightful article. He’s the Chief of Staff at the ecommerce startup Spring and one of the co-founders of the Chief of Staff Tech Network.

As Chief of Staff roles have become more ubiquitous at tech companies, my fellow tech chiefs and I have begun to have more frequent phone calls and coffee chats with people interested in learning more about the role and understanding how to go about landing a Chief of Staff gig — particularly with bankers and management consultants, who see it as an interesting path into the tech world. The most common questions I am asked are: what is the job like, how do I get a Chief of Staff role, and what should I be thinking about as I pursue tech chief opportunities?

Unfortunately, there is no one-size-fits-all description of what a Chief of Staff does. There is also no easy answer on how to get a Chief of Staff job at a growing tech company. But, as someone who has done the Chief of Staff role himself and has met with dozens of chiefs at other tech companies, I do believe there are a number of things that are important for you to keep in mind if you are thinking a tech Chief of Staff role might be your next step.

Let’s start with the good stuff:

  • No matter whether the role is predominantly administrative or highly strategic, you will learn a ton about what it is like to be a CEO. The job descriptions will vary, but one way or another the vast majority of tech Chief of Staff roles will give you a first-hand look into all of the major decisions your company is facing. It is a unique, potentially once-in-a-lifetime vantage point. Not only will you be able to observe your CEO processing his or her options in real-time, but you will potentially become a trusted advisor who can play an active role in shaping the direction of the company as well.
  • You will interact with all the departments and leaders in your company. As Chief of Staff, you’ll get exposure to marketing, sales, operations, engineering, all of it. That will enable you to develop relationships with people on teams you may not have worked closely with otherwise and help you hone in on what job functions you could really see yourself pursuing next.
  • The exposure you will have to what is going on across the entire business will help you determine what the best opportunities are for you to grow your career within your company. Is your company thinking about launching a new business line? Maybe you are beginning to discuss expanding internationally. Or perhaps there is a major new project coming down the pike. As Chief of Staff, you’ll know about all of it and likely be part of the strategy conversation. You’ll be in a perfect position to raise your hand and volunteer to get involved with, or perhaps lead, some of these new and exciting projects.

Now for some of the negatives:

  • It is a hard role to transition out of. If you move into a new role internally, it very likely could be perceived as a step back. You may find something amazing that will help you grow as a professional, but you need to be mindful that you will more than likely no longer be a direct report of the CEO. If you’re looking for a role externally, the job title is nebulous and it can be difficult for people at other companies to understand what skills you have and how you can contribute to their business. Many people have preconceived notions about what a Chief of Staff does, and those notions will not always be in your favor.
  • It is difficult to build a network. Yes, I know that is weird coming from the guy who helped start the Chief of Staff Tech Network, but hear me out. If you’re a digital marketer let’s say, you can meet your peers at conferences, you work with multiple agencies, and there is a common vocabulary that unites you with your fellow digital marketers. There’s none of that for tech Chiefs of Staff. Sure, you’ll get to know people across your own company, but you need to put the effort in to meet other chiefs and you are unlikely to really interface with people in more specialized job functions at other companies.
  • You will be a mile wide and an inch deep. If you’re looking at a Chief of Staff role as a chance to go deep and learn finance or marketing, for example, it’s not the role for you. Sure, the exposure you will have to all aspects of the business is great — and it will help you understand what you want to do next — but the Chief of Staff role is more than likely a jumping-off point to a job that will enable you to gain deeper subject matter expertise.

I have had an incredible experience as Chief of Staff to the CEO of Boxed. I have gotten to work for a visionary leader and have learned more than I ever could have imagined about how to start, grow and lead a company. But the role is not necessarily the right fit for everyone, and it is important to go in eyes wide open.

Should you decide that being Chief of Staff at a tech company is indeed the role for you, my number one piece of advice to you — besides reading every word of this post, of course — is this: make sure you have a clear understanding, straight from the CEO, of what exactly your role will be and how he or she will empower you to succeed. If you feel good about the answer, and you like and respect the CEO (that’s important!), I can guarantee you it will be a positive experience. If not, look elsewhere.

Still have questions on what it’s like to be a Chief of Staff? Email me at max.dworin@gmail.com.

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We are a collective group of operators serving a unique function of our respective businesses; the Chief of Staff. Join us as we share stories, lessons, thoughts and ideas of the CoS role and challenges faced building technology companies from the ground up.

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Max Dworin

Max Dworin

Food, Bev, CPG, Startups. Launching a new alcohol brand soon. Pursuing my MBA @yalesom. Formerly @BoxedWholesale & @SenSchumer. @Mets fan & @JohnsHopkins alum

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