The exercise window after you leave

Vested options are the right to purchase shares — a right your grant usually attaches to your employment. Leave, and most plans give you a limited period to exercise what you've already earned. Ninety days after your last day is the common default, inherited from a condition ISOs must satisfy to keep their tax treatment.

Exercise inside the window and the shares are yours, subject to whatever restrictions apply. Miss it and the vested options expire. Years of vesting can end with nothing, not because the company failed but because a date passed.

The window opens at the least convenient moment — while you are changing jobs — and it demands cash. Exercising means paying the strike price on every share you want to keep, and for options granted years ago against a much higher current estimated price, an ISO exercise can create an alternative-minimum-tax bill on top of the purchase, for shares you may not be able to sell.

Nobody sends a reminder. The grant document said ninety days; it said so before you had any reason to care.

Some companies deliberately extend the period — five or ten years is the usual alternative — specifically so that leaving does not force the decision. It is a real difference between employers and worth knowing about your own plan.

There is a trade-off written into the tax code: extending an ISO beyond ninety days generally converts it to an NSO, changing how an eventual exercise is taxed. Companies that extend do so knowing this.

ExitCue records the window length on each option grant and turns a departure date into a dated deadline you can see, with reminders ahead of it. The date comes from your plan terms as entered or parsed from your documents.

An exercise estimator inside ExitCue models what acting within that window would cost — the cash required and the tax it may create — using values you choose.