Introduction

Two offers with the same “headline comp” can diverge massively after you read the fine print. The biggest levers hide in vesting mechanics, refreshers, cliffs, exercise windows, and acceleration. This guide gives you a simple model and respectful scripts so you see the real number—and nudge it upward.

1) Inventory the terms (20 minutes)

Create a one‑sheet: Company | Level | Base | Bonus % | Equity Type (RSU/ISO/NSO) | Grant Size | Vesting | Cliff | Refreshers | Exercise Window | Expiration | Relocation/Sign‑On Clawbacks | Non‑compete.

2) Decode vesting and cliffs

• Standard: 4 years, 1‑year cliff, then monthly/quarterly vest.

• Impact: The first 12 months vest nothing; leave at month 11 and you get zero.

• Negotiable: sometimes shorter cliff or front‑loaded schedule (e.g., 10% year 1, then monthly) for senior roles.

3) Understand equity types (high level)

• RSUs: taxed at vest; simpler; often public/late‑stage.

• ISOs/NSOs (options): right to buy at strike price; potential AMT/ordinary income issues; value depends on exit.
  Ask for a 409A/last round price to sanity‑check options’ potential.

4) Refreshers—the quiet comp engine

Annual/quarterly refresher grants maintain your ownership as you vest down.

• Clarify cadence, target size, and performance link.

• Negotiate an initial refresher review at 12 months; even a small guaranteed band can offset a tight initial grant.

5) Acceleration (single vs. double trigger)

• Single‑trigger: vests more equity at change‑of‑control (rarer).

• Double‑trigger: acceleration if acquired and you’re terminated or materially demoted.
  Ask for X months of acceleration or at least pro‑rata vesting through notice period if your role is eliminated post‑acquisition.

6) Exercise windows & post‑termination

Options often expire 90 days after you leave. Longer post‑termination exercise (PTE) windows (e.g., 6–12 months) de‑risk your cash flow. If they won’t extend PTE, ask about early exercise with 83(b) eligibility (if appropriate)—talk to a tax pro first.

7) Clawbacks you should surface

• Sign‑on / relocation: what happens if you leave within 12–24 months?

• Repayment schedule: pro‑rated or all‑or‑nothing?
  If harsh, negotiate a pro‑rata payback or a shorter commitment window.

8) Model total comp over time (45 minutes)

In a simple sheet, rows by Month 1–48:

• Base/12, Bonus/12 (if target), Equity/12 (RSU) or Expected Value for options (conservative).

• Add a refreshers row starting Month 13.

• Flag cliffs, acceleration scenarios, and PTE constraints.
  Create three scenarios: Base Case, Bear (−30% equity value), Bull (+30%). Choose with eyes open.

9) Scripts to tune terms (respectful and specific)

• Refreshers:
  “Given scope and expected impact, could we set a 12‑month refresher target band? Even a range helps me compare fairly.”

• Cliff / front‑load:
  “Would you consider a 6‑month cliff or a slightly front‑loaded vest in year one? It aligns incentives as I ramp.”

• Acceleration:
  “Could we add double‑trigger acceleration of X months to de‑risk a change‑of‑control?”

• PTE window:
  “If options are offered, is a 6–12 month post‑termination exercise possible? It removes financing pressure.”

10) Ask the quiet questions (calmly)

• Any repricing or refreshers in the last 24 months?

• Average promotion timing to next level?

• Are refreshers automatic bands or manager‑discretionary?
  Answers here dramatically change expected value.

11) Red‑flag review

• RSU vesting tied to performance metrics without clarity.

• Non‑compete that’s broad in geography/scope.

• One‑sided IP/consulting clauses if you build side projects.

• Severance silence at senior levels—ask for a template.

12) Put it in writing

Verbal promises don’t vest. Request a revised written offer (or comp letter) with every term: refresher cadence, acceleration, PTE, clawbacks, review dates.

13) After you sign (protect the upside)

• Schedule a comp check‑in at 6 months.

• Keep a wins log tied to business metrics; it fuels refresher/promo reviews.

• Track vesting/blackout windows; plan vacations around cliffs if it matters.

Pitfalls

Comparing only “grant size,” ignoring cliff math, assuming refreshers happen magically, missing clawbacks, forgetting tax/AMT implications, or accepting “we’ll review later” without dates.

The compounding effect

You don’t need everything—two or three tuned clauses can add six figures over four years. The best part: these gains come from reading carefully and asking clearly, not heroics.

Bottom line: See the whole chessboard. Model the fine print, negotiate a few quiet levers, and lock them in writing.