Vesting and acceleration

Standard startup vest: 4 years, 1-year cliff, then monthly (sometimes quarterly). Leave at month 11 → usually 0 vested. Day 365 → 25% vests; then about 1/48 of the grant per month.

Cliffs protect the company from a hire who leaves after three months with a permanent cap-table passenger. They also create a sharp retention cliff at month 12: people sometimes stick unhappily until the cliff, then leave. Refresh grants and real scope growth matter more than trapping people until day 365.

The big idea

Refresh grants are new options issued later so you are not fully vested and walking. Common at growth companies; not guaranteed — ask. A refresh of 25–50% of your original annual run-rate is a different promise than "we will take care of you." Get timing and size in writing when you can.

Acceleration speeds vesting on events:

• Single-trigger: vest on change of control alone (less common for employees; more for some founders and executives)
• Double-trigger: vest if acquired and you are terminated without cause (or quit for good reason) within a window — the employee-friendly norm in many M&A deals

Negotiate acceleration seriously for senior roles; for IC offers it is often "company standard." Milestone or performance vesting shows up in executive packages and sometimes sales roles. Pure time-based vesting remains the default for engineers because product outcomes are shared and hard to attribute cleanly.

Walking through a year

Grant: 48,000 options, 4-year vest, 1-year cliff, monthly thereafter.

Month 11:  0 vested
Month 12:  12,000 vested (25% cliff)
Month 18:  12,000 + (6 × 1,000) = 18,000 vested
Month 48:  48,000 vested

If the company is acquired at month 18 and you are fired without cause, double-trigger (if you have it) can vest some or all of the remaining 30,000. Single-trigger would have vested them on the deal even if you kept your job. Read the grant agreement.

Common mistakes

• Leaving at month 11. The cliff is real; "almost a year" is still zero.
• Assuming a refresh. It is a new grant, not an automatic rider on the first one.
• Confusing single- and double-trigger. Sale alone vs sale-plus-termination.

Check yourself

You have 48,000 options, standard 4-year monthly vest after a 1-year cliff. You resign on day 360. How many are vested?

Zero. The cliff has not hit.

A deal closes and you keep your job. Does double-trigger accelerate you?

No. Double-trigger needs the sale and a qualifying termination (or good-reason quit) in the window.

Key takeaways

• Standard vest is 4 years with a 1-year cliff, then monthly.
• Refresh grants are new promises — ask for size and timing in writing.
• Double-trigger is the usual employee acceleration; single-trigger is rarer.
• The grant agreement beats the recruiter's email.

Further learning

Next, turning vested options into shares: exercising options.