Earlier quoted context omitted.
Yes, all former employees (current employees that hold RSUs are offered sell-to-cover, no worries on upfront tax by cash). And yes, they are RSUs. As for options, ex-employees need to pay to buy options when leaving the company within 90 days.
Well, for options it's more complicated than that - you can have ISOs that convert to NSOs to allow people to defer having to exercise illiquid options when they leave the company. So that's where my options question was coming from - the scenario you describe is VERY common in a scenario where ISOs have converted to NSOs upon leaving the company. But okay, you have RSUs - how familiar are you with your agreement? It…
Exactly this.
> If that's the case, they likely baked in a process for employees to have those shares withheld, or auto-sold during the lockup period. It's all tied in with their HR system and other payroll processes to make that easy.
In the agreement, they said this is up to the company, and the company chose the "pay tax to me or forfeit" option.
> There are companies that will loan you money to cover vesting costs or these types of situations - they'll do it at shitty rates, but if the options are losing out on a windfall or losing an extra 10-20% on the windfall, it's worth considering.
Thanks for this advice. Agree that this seems like a viable approach. Appreciate it!