How long do I have to exercise my vested options after I leave?

Standard is 90 days. Some companies offer longer windows (6 months, 1 year) as a benefit. After the window closes, unexercised options expire. This is a critical detail in your agreement.

Can I negotiate a longer exercise window?

Yes, especially in executive offers. Push for 6 months minimum, ideally 1 year. Some companies offer "extended exercise windows" as a retention perk.

What is the difference between ISO and NSO?

ISOs (Incentive Stock Options) can get favorable long-term capital gains tax treatment if held 2+ years post-grant and 1+ year post-exercise. NSOs are taxed as ordinary income when exercised. Your agreement should specify which type.

How long do I have to exercise my vested options after I leave?

Standard is 90 days. Some companies offer longer windows (6 months, 1 year) as a benefit. After the window closes, unexercised options expire. This is a critical detail in your agreement.

Can I negotiate a longer exercise window?

Yes, especially in executive offers. Push for 6 months minimum, ideally 1 year. Some companies offer "extended exercise windows" as a retention perk.

What is the difference between ISO and NSO?

ISOs (Incentive Stock Options) can get favorable long-term capital gains tax treatment if held 2+ years post-grant and 1+ year post-exercise. NSOs are taxed as ordinary income when exercised. Your agreement should specify which type.

AI Contract Analysis

Stock Option Exercise Agreement — Exercise Your Options Before They Expire

When you leave a job, you have a limited window (often 90 days) to buy your vested stock options before they expire forever. But your exercise agreement can have surprises: limited exercise windows, unfavorable pricing, and restrictions on transferring options. Our AI shows you exactly how long you have to exercise and flags aggressive terms that force you to act quickly.

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