Can we negotiate faster vesting?

As founders, sometimes — 3-year vest with 6-month cliff appears occasionally, especially for repeat founders or in competitive rounds. Employees: rarely, unless replacing a mature stock package from a public company.

What happens to unvested shares if we leave?

The company has the right (usually the obligation) to repurchase them at original cost. They return to the option pool for future grants.

Should we early-exercise our options?

If the company allows it and you have the cash: often yes. Early exercise + 83(b) election starts the capital gains clock immediately, potentially saving significant taxes at exit. Consult a tax advisor before doing this.

Vesting Schedule: 4-Year, 1-Year Cliff, Acceleration

Vesting protects the company from early departures walking away with equity.

Vesting Schedule: Standard Terms and Founder Considerations

Vesting is the mechanism that earns equity over time. Founders and early employees receive shares or options that vest according to a schedule — leave before vesting completes and you forfeit the unvested portion. The 4-year vest with 1-year cliff is nearly universal.

The 4-year, 1-year cliff standard

25% vests at month 12 (the cliff), then 1/48th monthly for the next 36 months. Leave before month 12: zero vested. Leave at month 24: 50% vested. This is standard for founders and employees at seed through Series C. Investors will require it at the first priced round if founders don't already have vesting.

Acceleration: single vs. double trigger

Single trigger: vesting accelerates on a change of control (acquisition). Rare for founders, more common for early hires. Double trigger: vesting accelerates only if there's a change of control AND the employee is terminated without cause. Standard for founders; increasingly standard for executive hires.

Founder-specific considerations

Credit for time served: if you've been building for 12+ months pre-financing, negotiate for that time to count toward the vest (starts you 25%+ vested at close). Repurchase price: if you leave, the company can repurchase unvested shares at original cost (not fair market value) — standard and reasonable.

Advisor and consultant vesting

Standard: 2-year vest with monthly vesting (no cliff), because advisor relationships often end informally. Grants: 0.1-0.25% for a genuine advisor commitment (monthly meetings, network intros, specific asks). Larger grants require operator involvement, not advisor status.

Frequently asked questions

Can we negotiate faster vesting?: As founders, sometimes — 3-year vest with 6-month cliff appears occasionally, especially for repeat founders or in competitive rounds. Employees: rarely, unless replacing a mature stock package from a public company.
What happens to unvested shares if we leave?: The company has the right (usually the obligation) to repurchase them at original cost. They return to the option pool for future grants.
Should we early-exercise our options?: If the company allows it and you have the cash: often yes. Early exercise + 83(b) election starts the capital gains clock immediately, potentially saving significant taxes at exit. Consult a tax advisor before doing this.