How to find and crush a job as a startup Chief of Staff

"So basically, Christian’s only skill is replying to emails faster than anyone else, at any time of day."

My brother-in-law has a way with words.

Over the holidays, I was explaining my role as the Chief of Staff at a Series C startup to my fiancée’s family and he interjected:

So basically, Christian’s only skill is replying to emails faster than anyone else, at any time of day.

My first thought was, understandably, “ouch.” But my second thought was that he wasn’t too far from the truth — because the Chief of Staff role is best understood as a service role.

This reality is often forgotten due to the sexiness of the title. Many young, ambitious folks with Main Character Energy actively covet the “Chief” title, and I’ve found that some have serious misgivings about what the role entails.

In this article, I’ll share what I’ve learned from two years on the job. I hope to help you find, land, and crush a job as a startup Chief of Staff — or, just as helpfully, to convince you that it’s not quite the job of your dreams.

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While preparing for my role two years ago, I read tons of CoS primers and disliked nearly all of them.

Perhaps the lone exception was an account from U.S. Army General (Ret.) Stanley McChrystal:

I wiped the dust off my uniform as I entered our Special Operations headquarters in Iraq. After walking 200 feet from the room I’d called home for the better part of five years, I was covered in the powder-like sands of the Iraqi desert. We were under the thick blanket of a haboob, a fierce and unforgiving sandstorm that had arrived without notice and cut visibility down to just a few feet. 

This was the worst of days for a sandstorm to arise. I needed to take a helicopter to Baghdad… [but] no aircraft could fly in these conditions, and our travel plans were now impossible.

“OK, Sir, here’s the recommendation…” I was greeted by my Aide de Camp, Chris Fussell, as I walked in. He’d been up for several hours, talking with pilots, synchronizing with the staffs of other senior leaders, and looking at key tasks that I needed to accomplish. The unexpected sandstorm had ruined several days of planning, so Chris had reviewed what the impacts were, rescheduled the day based on the known priorities, and put a new plan together…

What would have taken three hours of thought and coordination on my part was over in less than five minutes. The seamless reprioritization of the day before I’d even arrived was the sign of an informed staff, and of the effectiveness of [my] Chief of Staff.

While the analogy to military/political Chiefs of Staff isn’t always informative— I read The Gatekeepers and learned next to nothing — McChrystal’s account of a CoS resonated with my experience.

Over my last two years in the role, I’ve worked on tasks big and small: from building our Series C deck to ordering COVID tests for the office, from backfilling our VP of Operations when she was on maternity leave to taking notes at weekly meetings, and from leading a search for a new executive to literally taking out the trash.

(My Googling of “businessperson taking out the trash” was surprisingly fruitful.)

Chiefs of Staff are asked to execute a wide variety of tasks, and finding Full-Stack Businesspeople that are up for the challenge can be hard.

An additional challenge is that the folks who actually are broadly competent at most business tasks — like former consultants — don’t tend to be low-ego, roll-up-your-sleeves operators. They want to do ~*~strategy~*~, they want to delegate, they want to offer frameworks for key decisions. In fewer words, they believe that they’ve paid their dues and want someone else to do the grunt work — and such people would make terrible Chiefs of Staff.

While being a Chief of Staff will get you access into the Executive “room where it happens” and you’ll likely get some cool stretch opportunities, you can’t go into the role expecting sexy, high-level responsibility to be the norm.

To be a great Chief of Staff, you’ll have to operate at all levels of the organization: holding your own in executive conversations and efficiently cranking through a massive quantity of menial tasks.

Some examples:

• As an operator, you’ll sometimes serve as an assistant to the CEO (e.g., printing out documents) and other times as the independent lead of a strategic project (e.g., setting up a new business unit)

• As a communicator, you’ll sometimes have to listen carefully (e.g., note-taking to capture action items) and other times to speak authoritatively (e.g., explaining a new policy to the company)

• As a team leader, you’ll sometimes serve as a project manager (e.g., getting weekly status updates) and other times serve as an executive guide (e.g., helping a new exec onboard to the team)

• As a strategist, you’ll sometimes look like a carrier pigeon (e.g., defending a decision that was already made) and other times like the White House Chief of Staff (e.g., setting the agenda for key execs)

All of those examples are tasks that I have personally completed, or that I’ve heard of my Chief of Staff friends at other last-growing startups personally completing, and they’re broadly representative of the wide variety of work that a Chief of Staff can be tasked to complete. Long story short: if you’re looking for a daily diet of sexy responsibilities, stay away from the Chief of Staff role.

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💼 Three tips to find a great role as a Chief of Staff

1️⃣ Make sure your expectations are aligned with those of your CEO.

In the interview process, ask them what kind of support they want from you, and where they get that support today. You can ask them whether they think of the CoS role as a supplement or a complement (i.e., as someone who works with the CEO on the same tasks, or as someone who does different tasks to take them off of the CEO’s plate). You should also ask about any special projects that they’d like you to take on.

2️⃣ Sell yourself in the interview as an operational, not a strategic, whiz

There is little you can say in an interview to convince someone that you’re a brilliant strategic mind — it’s just not a fair fight. The CEO has so much more context about the business and the market than you do, so it’s more likely that your recommendations will come across as naïve than brilliant.

I’ve written about this before, and all of this advice applies to the CoS role:

What startups want from business hires

3️⃣ Do your damndest to find folks who can personally vouch for you in support of your application.

Unfair as it may be, many of the Chiefs of Staff that I know have some sort of personal connection to their CEO. The reason why is simple: you’re about to get business-married to your executive as a Chief of Staff, and knowing all the pre-martial stuff like their preferences and working style is important for mutual happiness in the pairing. You don’t want to commit to spending hours on the phone/in an office each day with someone you’ve just met; picking a Chief of Staff is a lot like picking a co-founder, so having a pre-existing relationship can be a huge benefit for both parties.

Assuming you don’t have any buddies who are CEOs of hyperscale startups, however, there’s still a ray of hope: you just need to find someone who can vouch for your character, ideally someone who the CEO already knows. As one example, the Chief of Staff role tends to be a 18-24 month role. If you befriend a Chief of Staff, then, perhaps they can be such a character reference for when a CEO looks for CoS #N+1. (May my inbox rest in peace.)

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💪Three tips for crushing your early days as a new Chief of Staff

1️⃣ Your top priority upon entering your role is to build credibility and trust.

I had a huge advantage when I started my role as Astranis’s Chief of Staff: I had already spent a year at the company, and had proven in that year that I was both competent and trustworthy. Chiefs of Staff that enter their organization from the outside, however, don’t have that luxury.

Successfully navigating the demands of the CoS role relies on your ability to have productive working relationships across all levels of the company. You want people to trust you enough to tell you what they really think, and to trust that you’ll follow through when you make a commitment to them. (This is particularly true for non-technical people at engineering-heavy companies.)

Work hard in your first days and weeks to prove to people that they can trust you. Work around the clock, if that’s what takes to get a few Ws on the board early. I promise: it’ll pay dividends in the long term.

2️⃣ Focus less on your own strengths and weaknesses, and more on those of your executive team.

As noted above, executives think of their Chiefs of Staff sometimes as complements and other times as supplements — but the correct answer is, of course, that there will be times when you’ll have to fill both roles. The key is knowing which role you’re playing.

To develop that awareness, you’ll need to be a great listener and a humble learner. You’ll also have to have a lot of conversations, especially if you’re new to the company. You ultimately want to know who in the organization is the best (and the worst) at every kind of task; doing so is instrumental to being an effective supporting cast member who can make the star exec shine, no matter the task or the exec in question.

3️⃣ Absorb, absorb, absorb.

Being the Chief of Staff at a fast-growing company is an incredible opportunity. So drink it in.

You’ll get plenty of advice from people to make sure that your CoS role lands you in a sweet [high-titled] role at your company, and (as a ambitious young person with Main Character Energy) you’ll wonder how the CoS experience can set you up for the rest of your professional life.

But, as someone with a few years of Chief of Staff experience under his belt, I’ll give you (and, I suppose, myself) some simple advice: cherish your time in the role. It’s more fun to savor experiences as they happen, than to cherish them once they’re gone.

So, enjoy yourself. Soak up everything that the early-executive access has to offer. And let me know once you do so — I’d be incredibly happy to hear if my words help you find, land, and enjoy your role as a startup Chief of Staff.

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Thanks for reading Silicon Valley Outsider! I’m Christian, the Chief of Staff of Astranis, and I write this newsletter for folks who are interested in startups but live outside of the SF Bay Area.

If you want to join 500+ folks in getting an email from me each Monday, I’ll help you understand Silicon Valley using normal-human words.

Here are a few past editions that you might like if you enjoyed this one:

• 😱 Don’t be afraid of working at a startup

• 💼 How to find a business role at a startup

• 🚀 The many, varied stages of startup life