| name | equity-design |
| description | Use when designing equity grant programs — covers grant philosophy, vesting, exercise windows, refresh, and exit considerations. |
Equity Design
Strong Legal Caveat
Equity is one of the most legally and tax-sensitive areas in HR. Every consequential decision requires employment counsel, securities counsel, and a tax advisor. The agent flags; specialists decide.
Grant Philosophy by Stage
| Stage | Pattern |
|---|
| Seed–Series A | Front-loaded; large grants; smaller team gets meaningful ownership |
| Series B–C | Mixed; decreasing % per role; refresh becomes important |
| Series D+ / pre-IPO | Smaller %, more dollar value; refresh annual |
| Public | RSUs; smaller %; market price drives value; annual refresh |
Document the philosophy. Communicate it to candidates and employees.
Vesting
Standard convention: 4 years total, 1-year cliff (no vesting until 12 months, then 25%, then monthly).
Variants:
- 4 years, 1-year cliff, monthly thereafter (most common)
- 4 years, 6-month cliff (more recent variant)
- 25/25/25/25 annual
- 5 years (Amazon-style back-loaded)
- 3 years, no cliff (sometimes for senior hires)
Convention is convention, not law. Match the vesting to the role and need.
Post-Termination Exercise Windows
The 90-day post-termination exercise window for options is convention, not legal requirement.
It disadvantages long-tenured employees: they have to come up with cash (and AMT for ISOs) to exercise within 90 days or forfeit vested shares.
Strong recommendation: extend to 7 or 10 years post-termination. Pioneered by Pinterest, Asana, Quora; increasingly common.
Caveat: ISOs convert to NSOs after 90 days post-termination (tax treatment changes). Document this clearly.
ISO vs. NSO vs. RSU vs. Restricted Stock
Strongly summary-only; consult tax advisor.
| Type | Tax at Grant | Tax at Exercise/Vest | Notes |
|---|
| ISO (US only) | None | Spread potentially AMT | $100k/yr cap; favorable LTCG if held |
| NSO | None | Ordinary income on spread | Broader applicability |
| RSU | None | Ordinary income on vest | No exercise; standard at public |
| Restricted Stock + 83(b) | Pay tax on grant value | None at vest | Cash outlay at grant |
Errors are expensive and often permanent. Get qualified advice.
409A and Strike Price
US private companies: strike price = 409A FMV (independent valuation).
Implications:
- Annual valuation typical; updated after material events
- Can't grant below 409A
- Strike rises as company values rise
- Errors create severe employee tax liability
Refresh Grants
Why:
- Original grant runs out (4 years)
- Market value has diverged
- Role grew beyond original level
- Retention concern
Design:
- Annual refresh (typical at growth+): smaller annual grants with own vest
- Performance-tied: ties to rating; risky if not calibrated
- Anniversary refresh: at year 3 or 4 to bridge cliff
Common failure: refresh ignored until employee threatens to leave. Reactive refresh = broken system.
Equity at Funding Rounds
- Down rounds: employee equity dilutes; refresh budget often increased
- Up rounds: equity becomes more valuable; refresh philosophy holds
- Recapitalizations: employee equity often hit hardest; counsel essential
- Bridge rounds: signal of trouble; equity programs often paused
Equity at Exit
- Acquisition: vesting often accelerated (single trigger / double trigger). Read the docs.
- IPO / direct listing: lockup periods (180 days typical); insider trading windows
- Tender offers / secondaries: opportunity for employees to monetize; eligibility varies
Communicate clearly to employees in advance. Surprises at exit are bad for trust and bad for retention.
ESPP
Employee Stock Purchase Plan (post-IPO): allows employees to buy stock at a discount (typically 15%) via payroll deduction.
Strongly favorable for employees. Recommend for all qualifying public companies.
Equity Communication
Most employees don't understand their own equity. Solutions:
- Annual statement: vested vs. unvested, current 409A, scenarios at multiple exit valuations
- Pre-funding-round comms: how the round affects existing grants
- Education programs: how equity works, tax basics
- Tax-prep resources during exercise events
Common Failures
- No equity philosophy
- Vesting mismatched to need
- 90-day exercise traps
- Refresh ignored
- ISO/NSO tax mistakes
- 83(b) elections missed
- Equity grants employees can't model
- Acquisition surprises
- Recapitalizations that hit employees disproportionately
Cross-References
equity-architect agent
compensation-strategist agent
compensation-philosophy skill
legal-and-jurisdictional-boundaries rule
Key References
- Holloway Guide to Equity Compensation (Levy & Wallin)
- Industry practice from Carta, Pulley, Compensia
- IRS guidance on Section 422 (ISOs), 409A