re: Employer acquired, want to be let go

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The only answer is that he can't have his cake and eat it.
He should

1) either stick around for the stock vesting (oh and this never ends btw, the pile keeps getting bigger and bigger) making it more difficult each year

2) look for a new job. It's not uncommon to work a deal with the new company for unvested shares. Obv won't be a 1-1

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Agree with castorinho.

The best leverage of all is to get a new offer and get them to cover some portion of the at-risk pay on the table in the current firm. Now, that's only likely to happen if you are a stellar candidate for a senior role at a large company.

It also matters how many RSUs are on the unvested table. Does OP have $200K unvested or $2M? If it's on the lower end then it's a pretty easy negotiation...a signing bonus and potentially some portion of RSUs on signing (with say a 2 year vest for retention at new company) can make-up most of this without the company really batting an eye. Plus, you can proibably get a base salary increase. Bigger question might be whether the ongoing RSU package at the NewCo will be at parity to current expectations or not (this can swing the decision criteria mightily).

If the OP is on a more extreme end of at-risk pay (the $2M unvested example), then the options really limit. Even a partial coverage of that amount will require you to be at a very senior role at NewCo (potentially a promotion versus the current position at OldCo). Executive comp packages have a lot more variables to them, so I won't begin to work through hypotheticals there.

At the end of the day, it's just work....if the OP is unhappy but getting paid well, then detach the emotion from the job and collect the paycheck. Otherwise, venture into the job market while you have significant leverage (a highly paid current position....no recruiter needs to know anything about happiness or RIF potential) and see what can happen.

ETA: The optimal outcome is a severance package that accelerates vesting of some portion while having the NewCo lined up. That's a very time sensitive plane to land unless OldCo does a 'call for retirements'....so while this is optimal financially, it's quite unlikely to be feasible.

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Acquaintance wants out bad

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he should accuse his manager of calling his wife a fish head and rubbing her cannons on him while he is trying to work