How soon after I hit my 1-year cliff can I quit?

Editor’s note: A version of this question originally appeared on Reddit.‍

I work at a small startup and will hit my 1-year cliff on my stock options on Dec. 2. If I quit my job on Dec. 15, will that impact my ability to acquire my shares?

- Anonymous

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Dear Anonymous,

Double- and triple-check your stock options paperwork. You’ll want to pay particularly close attention to your stock options grant date. If you were granted the shares on Dec. 2 last year, then you will have successfully reached your 1-year cliff on Dec. 2 this year, and should be able to exercise your stock options immediately.

As you probably know, most people only vest one-quarter of their stock option grant on their one-year cliff — for example, if you were granted 10,000 shares of stock options on a standard vesting schedule, you’d unlock the ability to purchase up to 2,500 shares at your one-year cliff.

Before you leave your job, review your stock options paperwork for your post-termination stock options exercise window. Most startup employees have just 90 days to exercise their stock options when they leave their job, or they risk losing their stock options entirely.

A small group of companies voluntarily offer longer post-termination stock options exercise windows, although you’ll want to check if there are any stipulations attached. For example, at some startups, you have to stay employed for at least two years before becoming eligible for the extended post-termination exercise window.

You’ll want to check too that you’re not in a stock options blackout window that prevents you from exercising your shares. This typically happens as a company is raising a new round of funding or is nearing an exit event, like an acquisition or IPO.

General advice that applies to all startup employees: Before you exercise your stock options, calculate your total cost to exercise (including taxes), and build a plan for how to pay for your options. We’ve built a handy Stock Option Tax Calculator that can help you model out your costs.

- Vieje Piauwasdy, Director of Equity Strategy, Secfi

Do you have a question about your stock options? Email us at ask@secfi.com

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