Interviewing for a chief of staff role at a startup that’s raised about $14M so far. What should I look for when assessing if this is a good opportunity?

Would work directly with CEO and expecting cash compensation of 100K and 0.25% of equity. Is the equity % low?

CEO hopes to sell at 100M, meaning the equity would be valued at 60K a year (4 yrs), but this seems optimistic to me.

2 YOE for reference.

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Understand what the role entails - are you more an admin or are you a strategic partner? Some execs see a CoS as an extension of their admin (if they have one). What is the trajectory of the CoS role? Is there an opportunity to roll into another role as the company grows or will you always be the CoS? You also want to understand what your key metrics will be and what ‘success’ is defined as.

You’ll also want to make sure that anything you have as a ‘package’ re: comp and equity are in writing and you’ll want some kind of caveat that if the company goes public, that the equity translates to stock equivalent.

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What you just listed sounds much more admin than strategic. Understand if that will be the majority of your workload and if you're ok with that type of work. At 2 YOE, it could be a great way of being in meetings to learn in the early part of your career. Any targeted exits mean very little with $14M raised. I would be more focused on revenue and growth rate than capital at this point.

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See at what valuation did they raised the last rounds - this can tell you a bit about how realistic are the 100M CEO is talking about.

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Chiefs of Staff are usually glorified secretaries, so be ok with that if you make the move. The ones at Bloomberg were all proxies for the group Presidents, but they didn’t make any independent calls of their own.

helpful

And that’s why I wrote “usually”. It is rare that the Chief of Staff is some valued member of the C Suite - especially if the firm has a Chief Strategy Officer, a COO and a CFO.

At Bloomberg they are lapdogs. At Bank of America they are secretaries.

So I can’t give any advice, but out of curiosity how did you find the role?

LinkedIn

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