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@OP- I think you need to look how does this role fit your long term career goal to get a better answer
On the comp, I would go back and try to get the signing bonus to make you whole over 5 year period and faster equity vest schedule.
5yr vesting seems really long. Is it at least some vesting each year or none until year 5? If the latter I’d be worried about annual salary increases - why would they give you fair annual increase if they think they can just keep you around waiting for that equity anyway?
All at 5 yrs. thats a great point on incentives...their benefits/401k are pretty bad too, so why would they improve them if everyone is locked in...
Sounds like a great opportunity but I wouldn’t be able to do it with that comp. how flexible are they with negotiations?
It seems like you are compromising on a lot for the experience. Which brings it down to how important is the experience and how much are you willing to trade for it?
Also, I would only really value this role on a 12 month basis, there are a lot of unknowns 5 year equity upside shouldn’t be a factor, yoy component should be.
Sounds like a lowball offer and with a lot of risks. The upside is unknow for a few years. Real operations experience is great and hard to get in an advisory capacity. There is a mis alignment on comp and risk/award. Wait for a better exit in a few years or negociate a better offer with an intention to walk.