1
Identify the parties and award type
Enter the company's full legal name, state of incorporation, and the recipient's full legal name and role. Specify whether the award is an ISO, NSO, restricted stock grant, or RSU, as this determines every tax and compliance consequence downstream.
💡 ISOs are available only to employees — if the recipient is a consultant, director, or advisor, the award must be an NSO regardless of how it is labeled.
2
Complete the 409A valuation before setting the exercise price
For any option grant in a private company, obtain a current 409A valuation from an independent appraiser before setting the exercise price. The exercise price must equal fair market value on the grant date for ISOs to qualify for tax benefits and to comply with IRC Section 409A for NSOs.
💡 A 409A valuation is typically valid for 12 months or until a material event (funding round, acquisition letter of intent) — use the most recent report and confirm it has not expired.
3
Set the vesting commencement date and schedule
Enter the vesting commencement date (which may precede the grant date if crediting prior service), the cliff period (typically 12 months), and the subsequent monthly or quarterly vesting cadence. Confirm the total vesting period and number of shares match the cap table entry exactly.
💡 Document the vesting commencement date in the agreement and in your cap table software simultaneously — discrepancies between the two are a leading source of disputes at liquidity events.
4
Define acceleration triggers precisely
Specify whether acceleration is single-trigger (change of control alone) or double-trigger (change of control plus involuntary termination within a defined window). Set the percentage of unvested shares that accelerate and whether acceleration applies to all award types under the plan.
💡 Double-trigger acceleration is strongly preferred by acquirers and institutional investors — single-trigger acceleration should require explicit board approval and documentation.
5
Complete the post-termination exercise windows
Set separate exercise windows for voluntary resignation (90 days is standard), termination without cause (90 days to 1 year), death (12 months), disability (12 months), and termination for cause (immediate expiration). Confirm that ISO windows do not exceed 90 days for employees or 12 months for disability.
💡 Some companies are extending post-termination windows to 5–10 years for NSOs to reduce the 'golden handcuffs' problem — this is a board-level decision that should be reflected uniformly across all grants.
6
Include the 83(b) election notice for restricted stock
For any restricted stock grant (not options or RSUs), include a prominently placed notice informing the recipient of the 30-day window to file a Section 83(b) election and the consequences of not filing. Attach a completed election form as an exhibit.
💡 Provide the recipient a pre-completed 83(b) election form and instructions for mailing to the IRS — the company cannot file on the recipient's behalf, but can dramatically reduce the risk of a missed deadline by making it easy.
7
Execute before the grant date
Both parties must sign the agreement on or before the grant date. Backdating option grants to a lower fair market value date is a securities violation. Use Business in a Box eSign to timestamp execution and store the fully-executed copy alongside the cap table record.
💡 Board approval of each grant (via board resolution or unanimous written consent) should be obtained before execution — the agreement should reference the authorizing resolution by date.
8
File required notices and update the cap table
After execution, update your cap table to reflect the new grant, issue any required securities law notices (e.g., Rule 701 disclosure for private companies exceeding the annual threshold), and confirm the grant is recorded in your equity management platform.
💡 Rule 701 under the Securities Act requires additional financial disclosure to recipients when aggregate equity grants in any 12-month period exceed $10 million — track running totals against this threshold in your cap table software.