Build a grant-to-exit timeline

Use distinct event types

Grant, vest, exercise, purchase, sale, tender, expiration, and termination are different events. Record date, shares affected, cash flow, tax question, required action, and source document.

A departure from employment can change the exercise window even when the stated option expiration is years away.

• Event date
• Shares affected
• Cash required
• Tax or filing question
• Action deadline

Model more than one path

Create timelines for continued employment, departure, no liquidity, a tender offer, and a sale where relevant. Do not assume the company will provide a future market or financing.

Review the timeline with qualified tax and legal professionals before acting on material amounts.