A jester holds court
An interview with @chiefofstuffs
@chiefofstuffs is a reliably acerbic presence on startup twitter, dispensing cynical/realistic takes on the tech ecosystem from an operator’s perspective. They were kind enough to answer some questions for us about the in-demand chief of staff role.
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How did the chief of staff title become so sexy?
The West Wing arrived on Netflix. IDK. CEO office has existed for ages, I guess what was interesting about the title is that it was actually unique within a company. There was only one person who could have that title. Of course, now you have Chief of Staff to the Director of Product, Ad Revenue and it's become completely useless as a heuristic.
How did you find your role?
I asked a bunch of VCs I knew for intros to different CEOs. I happened to click with a few and got to offers with a few. I was introduced to the concept by a guy who had a similar role; his philosophy was that you have a particular skillset; the way to avoid competition is to pitch that skillset to CEOs. Either they say "holy shit I need that" or "nah I don't need that'. In the latter case you can just move on. In the former case, if they're not already looking, then you have much less competition.
How has the fully-remote workplace changed the role of the CoS?
All the background work for cross-functional collaboration is substantially harder. One of my favorite techniques to get things done was the hallway/lunch interception and that's useless now.
What do people think chiefs of staff do vs. what do they actually do?
There's a wide range of activities for this title, from "business-minded EA" to "CEO's decisions are delegated". People can be impactful / high ROI in the entire range. Some days, the boss's EA is a lot more impactful than I am, and she's a lot cheaper too.
What you do a lot of depends on the neuroses of the particular CEO you work for. Mine was previously a management consultant so I spend a lot more time fiddling with slide alignment than I naturally would. It also depends on the needs of the company at the time. You don't really get to pick. I built our first sales reporting, started our incident response program, work on board/investor reporting, recruit, and even did an (email) interview posing as the boss. It really just depends.
There's typically a lot more PMO type activity than people would expect. I think a lot of people expect to be some sort of "strategic thinking partner" which definitely happens - but sometimes the boss really just needs someone to keep the trains running on time. Especially at a startup, there's not that much time for strategy and frankly it's not needed that much.
What are red flags to look for in CoS job descriptions?
The JD should be clear on what the role is within the range of possibility. Nobody succeeds if people come in thinking the job is one thing and it's another. It has also become a popular enough title that it's become more useless as a signal. Sparkling bizops, if you will.
If you were a CEO, would you hire a CoS?
At a certain stage (50+ employees), yes. Or promote someone internally. I think of it more as a tool you can use to recruit an ambitious IC into.
After the CoS role becomes blase, what's the next must-have job title?
We're probably circling back to GM / Special Projects / CEO Office / Bizops as CoS gets more diluted, but who knows? Technical advisor? Consigliere? Court jester?
Bonus question: for people looking to leave consulting/banking and weighing VC associate roles vs. CoS roles, what would you recommend?
Josh Kopelman of First Round recently said, a chicken and a pig are both involved in making breakfast. A chicken can lay lots of eggs, but the pig is much more committed. As an operator you are a pig. The jobs are massively different. They're only really roughly equivalent in terms of prestige, feeder pipeline, % of time being someone's gofer. If you care about prestige be an associate.
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