Most people only think about their equity twice: when they sign the offer and when they leave. The 48 vest dates in between pass silently. Set an email reminder for each one and give yourself a chance to actually make a decision before the next tranche lands.
Done in seconds. No sign-up required.
Not because it doesn't matter. Because nothing prompts a decision.
vest events in a standard 4-year monthly schedule after the cliff
12 months × 4 years, minus pre-cliff months
of employees say they don't fully understand the equity they were granted
Carta 2023 Equity Education survey
typical window to exercise vested options after leaving — miss it, forfeit it
Standard ISO post-termination rule
Vesting is invisible by design. Nothing arrives in your inbox on the day. No share certificate gets mailed. The company doesn't message you. Your equity platform updates the dashboard, but only if you log in. The new tranche becomes exercisable and then sits there, undecided.
Over a four-year grant that's roughly 48 missed decision points. Each one is a moment where you could check the current strike vs. fair market value, consider exercising early to start the long-term capital gains clock, or just register that you now have more equity than you did last month. None of that happens if no one reminds you.
The cliff is the only vest date most people actually notice, because it's the one their employer wants them to remember. The 47 after that are on you.
Pull your vesting schedule from your grant agreement or your equity portal (Carta, Shareworks, AngelList Stack, Pulley). Pick the dates that matter — the cliff, the monthly or quarterly anniversaries — and set a reminder a week before each. You can set them all in one sitting.
Check your grant agreement or equity portal. Note the grant date, total shares, cliff date, and post-cliff frequency (monthly or quarterly).
A week before each vest gives you time to check current share value, AMT implications, and your cash position. The decision is rarely urgent on the day itself.
BoldRemind sends advance notice, then a reminder on the day, then follow-ups if you haven't acted. The new tranche won't pass silently.
Three things to understand before the next tranche lands.
Standard is 4 years with a 1-year cliff, then monthly. Your cliff vests 25% in one chunk; the rest drips in 1/48ths after that.
How the schedule works →Vesting gives you the right to buy at your strike price. You still have to write the check (or do a cashless exercise) and pay any tax due before you own shares.
The three-stage journey →Given the grant date, total shares, cliff length, and frequency, you can figure out exactly how many shares are vested as of today. Spreadsheet or calculator.
The vesting formula →The details, one topic per page.
Vesting is only the first half of the equity timeline. Once a tranche is vested, you have a new set of deadlines: when to exercise, what tax bracket to land in, the 90-day post-termination window if you leave, and the 10-year expiration that ends the grant entirely.
See stock options exercise reminders for the exercise-side cluster — when to exercise, the 90-day post-termination window, and the 10-year expiration date.
Vesting gives you the right to exercise the options — to buy the shares at your strike price. It does not mean you own the shares yet. Until you exercise, you have a contract, not stock. That distinction matters for taxes and for what happens if you leave.
Set one for about a week before each vest date. That gives you time to check the current 409A or share price, look at your cash position, and decide whether to exercise the new tranche or wait. The vest itself takes one second; the decision around it takes longer.
Almost always, yes. The most common pattern is four years of vesting with a one-year cliff, then monthly or quarterly vesting for the remaining three years. Your grant agreement spells out the exact schedule. Senior hires sometimes get accelerated or back-loaded variations.
Standard schedule is four years total. The first 25% vests at the one-year cliff, then the remaining 75% vests over the next 36 months. Some companies use five-year schedules or front-loaded patterns, but four-year is the default in tech.
Not actively. Equity platforms display your vesting schedule and let you log in to check, but they do not send a proactive email on each vest date prompting you to make a decision. That gap is where vested equity sits ignored, sometimes for years.
Vesting is the company giving you the right to buy. Exercising is you actually buying. They are two separate events, often months or years apart. See the full explainer at /stock-options-vesting/vested-vs-exercised-difference/.
Yes, in two ways. If you leave the company, you typically have 90 days to exercise vested options or you forfeit them. And every option grant has a 10-year expiration — vested or not, if you do not exercise by then, the contract ends. Reminders matter for both deadlines.
Free. No account. Pull your schedule from Carta or your grant agreement, set a reminder a week before each vest, and stop letting tranches pass silently.
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