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1. Make sure you have some actual work and impact instead of being glorified overworked project manager for some CxO
2. Series b - it better be projected to be damn successful, coz you’re taking a pay cut so the real value is equity. I feel at series b it can be a bit risky and if it’s the worst case equity can be zero. Can you not at least put the money they cut from base as part of a bonus contingent on your performance? Or can they give you a joining bonus for now, and you can then push for a pay increase next year later?
3. What’s the clear path after CoS? Has leadership promised you they’ll let you move to a function of your choice at VP title or not? What do you want to lead at this company after CoS - this clarity is important and IMHO this is the real reason why EMs should go for chief of staff role for 1/2 years
4. What’s your current title going to be? Yes if it’s a startup and you exited in a year it may not mean anything, but I would make sure for a pay cut you had a title inflation. Nothing less than a Director at startup, Senior Director if you can manage it.
5. As CoS are you going to have direct reports or not (if not now, 6 months down the line). In industry, being a people manager matters and is valuable on resume
6. Do you “fit” with the CxO’s working style? Have you evaluated that
If 3-4 of 6 factors align, (and 2,3,4,6 are most important), I would go for it in your shoes.
Pro
This post is an example of what I meant by point 3 - having clarity on path after CoS
CoS is all over the place as a title and equity can also mean nothing depending on company stage… so hate to say, but it depends
Series B means your equity has at least some paper value but can still be easily zeroed out. Personally I would count on $0 from it. If you want a (largely meaningless) estimate of value, make sure you understand how many options you are being granted at what strike price and when AND what the rest of cap table looks like AND what the broader funding plan is (ie if they need outside capital for a while, each round will dilute the value of your equity)