In startup land, the "Chief of Staff" title can mean many different things. As we start the new year and many are assessing their next moves (and asking me for advice ), I thought I'd share my thoughts on the role, what's hard about it, & how to make the most of it.

THREAD

The typical rationale for hiring a Chief of Staff is to help an exec scale. This can mean many things, but generally an exec needs to get time back by offloading tasks that don't fit neatly into the current organizational structure of their team.

In my view, the CoS title can mean 3 things: 1) Executive assistant with outsized responsibility (50%+ of workload is administrative) 2) Special projects manager (usually similar to a strategy role) 3) Jack-of-all-trades / gap-filler / fixer

EA: you're likely a qualified EA with experience in this type of role in the past. This can be an awesome way to parlay prior experience into a different role. How to figure out if this is the CoS role you're interviewing for? Ask what % of your time will be spent on admin tasks.

Special Projects: you're likely an IB analyst, consultant, VC associate, or other similar job and you're looking for a role that will broaden your horizons. This is often at scaled cos (Series C+) where the CEO / exec team needs someone to work on high level strategy projects.

Jack-of-All-Trades: you're likely from a finance or consulting background or from another company where you've worked in strategy / operations. This CoS role is the least structured and essentially is a bandaid role: hire someone smart / scrappy who can help fix problems.

I'm generalizing here, but these are the rough buckets I've seen. Making sure you understand what you're signing up for is paramount to success. By asking clarifying questions you'll also help the person hiring you better understand what they want, because often they don't know.

How to make the most of the CoS role? First, most are explicitly 18-24 mos long, thus going in with a clear goal for what you hope to learn is key. For example, CoS roles are great for getting exposure to a broad array of functions and learning where you might fit longer term.

Second, attitude & approach matter. For example, if your goal is to learn how product & eng orgs run, make that clear from day 1. Go out of your way to meet people, volunteer for projects, and spend your "free time" pursuing that goal. The role is ambiguous, take advantage of it.

What's hard about the role? First, often execs hiring CoSs don't know what they want / need & don't realize that just hiring someone smart won't solve their problems. Execs can struggle to figure out how to utilize the new resource they hired and you may have to figure this out.

Second, the role is highly ambiguous both in terms of actual tasks that make sense for you to own and in terms of what KPIs you should be measured against. If you are someone that loves clear directives and goals, CoS may not be a great fit.

Third, it's hard to avoid stepping on toes. Often you're tasked with projects that span across multiple organizations and already have owners. If you've been sent by an exec to "fix" or "analyze" a process, this can lead to you being seen as foe vs. friend.

That said, CoS is an amazing role for anyone with a clear learning or career goal that they believe the role will solve and someone who is able to deal with ambiguity exceptionally well. It's a great way to spend time learning and growing without having to pick a specific org.

This is by no means comprehensive (it's a Twitter thread afterall), but I hope this is helpful. For me, the role was wonderful, I learned a ton and got access to so many people across the organization. I'm deeply grateful for my time @Zuora.

If you've been a CoS, what did I miss that's important when thinking about whether a role like this is a good fit?