← All workflows

Stock Option Grant

Draft Stock Option Grants in Minutes, Not Hours

12 minutes with CaseMark

Fast lane

We have it from here.

Choose the fast one-off run here, or jump into the workspace when you want saved history, revisions, and a fuller matter workflow.

Run this once here

Best for a quick one-off job. Add your email, upload the files, and we'll run the workflow and send the result to your inbox.

1. Add your email so we know where to send the result.

2. Upload the files you want analyzed.

3. Run the workflow and we'll take it from there.

Use in Workspace

Best for ongoing matters

Save and reopen matters, keep documents together, refine the output, rerun with changes, and export or share polished work product when you're done.

Open in Workspace

Need more context?

Scroll for the workflow details below if you want to review what this run handles, what documents help, and what the output looks like.

If this is part of a live matter, the workspace is the better fit: you can keep your documents together, revisit the result, and keep working without starting from scratch.

Jump to detailsOpen in Workspace

Start here

Run this workflow now

Best for a fast one-off run. Add your email, upload the files, and we'll deliver the result without sending you into the full app.

Workflow

Stock Option Grant

Step 1 · Deliver to

Step 3 · Run this workflow

Workflow

Stock Option Grant

Overview

CaseMark's Stock Option Grant skill drafts comprehensive ISO and NQSO stock option grant agreements that integrate seamlessly with a company's existing equity incentive plan. The AI handles vesting mechanics, exercise procedures, termination provisions, tax compliance under IRC §422 and §409A, securities restrictions, and change-in-control triggers — producing a complete, board-ready agreement from your uploaded documents.

Drafting stock option grant agreements manually requires careful coordination across board resolutions, equity incentive plans, employment agreements, tax code provisions, and securities regulations. A single oversight — such as an incorrect exercise price or missing savings clause — can trigger adverse tax consequences, securities violations, or costly disputes with departing employees.

CaseMark automates the drafting of stock option grant agreements by analyzing your equity incentive plan, board resolution, and recipient agreement simultaneously. The AI cross-references grant parameters against IRC §422, §409A, and securities requirements to produce a complete, compliant agreement ready for review and execution.

How it works

  1. 1. Upload your equity incentive plan, board resolution, and recipient agreement

  2. 2. AI analyzes grant parameters, option type, and compliance requirements

  3. 3. Review the fully drafted stock option grant agreement with all key provisions

  4. 4. Export the finalized agreement in your preferred format (DOCX, PDF)

What you get

  • Caption & Recitals

  • Definitions

  • Grant Terms & Vesting Schedule

  • Exercise Mechanics

  • Termination & Post-Termination Exercise

  • Tax Treatment & Withholding

  • Change-in-Control Provisions

  • Transfer Restrictions & Securities Compliance

  • Miscellaneous & Signature Blocks

What it handles

  • Automatic ISO vs. NQSO classification with IRC §422 tax compliance

  • Customizable vesting schedules with cliff and acceleration provisions

  • Termination and post-termination exercise period drafting

  • Change-in-control and acceleration trigger provisions

  • 409A valuation and FMV exercise price verification

  • Securities law compliance and transfer restriction clauses

Required documents

  • Equity Incentive Plan

    The company's adopted equity incentive plan, including any amendments, under which the option is being granted

    .pdf, .docx

  • Board or Committee Resolution

    The board or compensation committee resolution authorizing the grant, specifying grant date, share count, exercise price, and recipient

    .pdf, .docx

  • Recipient Employment or Consulting Agreement

    The optionee's current employment or consulting agreement, including any equity, acceleration, or post-termination provisions

    .pdf, .docx

Supporting documents

  • Certificate of Incorporation & Bylaws

    Corporate charter documents showing authorized shares, stock classes, and governance provisions

    .pdf, .docx

  • 409A Valuation Report

    The most recent independent 409A valuation establishing fair market value for private company stock

    .pdf, .docx

  • Cap Table or Stockholders' Agreement

    Current capitalization table and any stockholders' agreement with ROFR, co-sale, or drag-along provisions

    .pdf, .docx, .xlsx

  • Insider Trading or Equity Administration Policy

    Company policies governing insider trading windows and equity administration procedures

    .pdf, .docx

Why teams use it

Reduce drafting time from hours to minutes while maintaining precision across complex tax and securities provisions

Ensure automatic compliance with IRC §422 ISO requirements, §409A exercise price rules, and securities law transfer restrictions

Generate consistent, plan-integrated agreements that cross-reference existing employment terms and acceleration triggers

Easily customize vesting schedules, termination exercise windows, and change-in-control definitions for each grant

Questions

Can CaseMark draft both ISO and NQSO agreements?

Yes. CaseMark automatically tailors the agreement based on whether the grant is an Incentive Stock Option (ISO) under IRC §422 or a Non-Qualified Stock Option (NQSO), including the appropriate tax treatment, exercise price requirements, and savings clauses.

How does CaseMark handle vesting schedules?

CaseMark generates customizable vesting schedules including standard four-year vesting with a one-year cliff, monthly or quarterly vesting increments, and single- or double-trigger acceleration provisions tied to change-in-control events.

Does the output address 409A compliance?

Absolutely. CaseMark ensures the exercise price meets fair market value requirements under IRC §409A, references the applicable valuation methodology, and includes protective language to avoid adverse tax consequences for both the company and the optionee.

Can I customize change-in-control and acceleration provisions?

Yes. CaseMark drafts change-in-control definitions with configurable threshold percentages and supports both single-trigger and double-trigger acceleration, cross-referenced against the recipient's existing employment or consulting agreement.

What if the recipient is a greater-than-10% shareholder?

CaseMark automatically applies the heightened ISO requirements for greater-than-10% shareholders, including the 110% FMV exercise price floor and the five-year maximum option term required under IRC §422.

Does CaseMark include securities law provisions?

Yes. The generated agreement includes transfer restrictions, securities representations, legends, and compliance provisions addressing applicable federal and state securities laws, including Rule 701 and Regulation D considerations.

Related

30b6 Corporate Rep

Draft & Defend 30(b)(6) Depositions in Minutes

30b6 Deposition

Master 30(b)(6) Depositions in Minutes, Not Hours

Abstract of Judgment

Draft Judgment Abstracts in Minutes, Not Hours