[redshirtrob]

Be careful, the company may not be required to buyback the shares. The company may have the option to accelerate the vesting schedule on the options. It's best to assume they'll choose to do this only when it's optimal for them, which likely means when it's suboptimal for you.

[brianmcconnell]

It's a real dilemma, as the company is doing well enough that the 409a value is not trivial, but its not clear that they will have a liquidity event in the near term. So on one hand I don't want to get screwed on a fictional profit on taxes, but on the other I don't want to forfeit the options as I earned them, and as far as I am concerned, that was part of my compensation for taking below market salary.

It bothers me that the terms are unnecessarily anti-employee. 90 days simply isn't enough time, especially when critical details related to the cap table and liquidation preferences are obfuscated. If they are not prepared to buy shares back at 409a value, they should allow an extended exercise window.

[nraynaud]

Happened to me. (Not a big sum)