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5 Things to Read in Your Equity Grant Before You Sign (Most Candidates Miss 3 of Them)

The cash component of a tech offer in 2026 is increasingly the easy part to negotiate. The hard part is reading the equity grant — and most of the candidates I have helped negotiate offers in the last year did not realize how much they were leaving on the table because they did not know what to ask.

This post covers the 5 things to read in any equity grant before you sign, and the questions to ask if the offer letter does not address them. None of this is legal advice; it is the practical version of what someone who has been on the receiving end of half a dozen of these now would tell themselves before round 1.

1. The grant size, and what it is worth at four different prices

The offer letter says "150,000 RSUs" or "0.4% equity." That is not the negotiation surface. The negotiation surface is dollars, and dollars require a price.

For RSUs at a public company, ask for the 30-day trailing average share price as the basis for the dollar value, not the strike or the day-of-grant price. The day-of-grant price is what most companies use; the trailing average is more honest because it smooths out a bad day.

For private-company stock or options, ask the recruiter to walk you through the math at four different exit valuations:

  • Bear case (50% of last round price)
  • Last round price (the most common reference point)
  • 2x last round price (the company's near-term aspiration)
  • Bull case (5x or 10x last round, depending on stage)

If the recruiter cannot or will not do this math with you, that is a signal. The number on the offer letter is meaningless without the math.

2. The vesting schedule (and the cliff)

Standard is 4-year vesting with a 1-year cliff. If your offer is anything different, read it carefully:

  • 5-year vesting: rare, almost always worse for you. Push back to 4-year.
  • No cliff: good for you, ask if the recruiter offers it (some do, some do not).
  • Back-loaded vesting (10/20/30/40 over 4 years): common at Amazon and a few others. The dollar value of the offer is meaningfully lower than a 25/25/25/25 schedule. If the offer letter does not specify, assume 25/25/25/25 and ask explicitly.
  • Monthly vs quarterly vs annual cliff: ask. Monthly is best for you. Annual is the worst (you lose 11 months of vesting if you leave 11 months in).

3. The strike price and the 409A timing (private companies only)

For options at a private company, the strike price is set by a 409A valuation that is updated periodically (usually annually, sometimes more often after a fundraise).

Ask:

  • "When was the most recent 409A valuation?"
  • "Is there a fundraise that might trigger a new 409A before my grant date?"

If a new 409A is coming and it is going to raise the strike, your effective gain on the grant just dropped before you started. You can sometimes negotiate the grant date to before the new 409A, or negotiate more shares to compensate.

4. The post-termination exercise window

This is the one nobody warns you about and it has cost real people real money. When you leave a company with vested options (private company), you typically have 90 days to exercise them or you lose them.

Ask:

  • "What is the post-termination exercise window?"
  • "Is there an extended exercise window for employees who stay 2+ years?"

Some companies (Stripe, Pinterest historically, several more) offer extended windows (up to 10 years) or convert vested options to RSUs in some scenarios. Some do not. The difference can be six figures of value depending on your tenure and the strike price.

If the company has a 90-day window and refuses to extend it, factor that into your decision: your vested options are essentially company-controlled until you exercise. Exercising can be expensive (especially with AMT implications in the US), so the options can be effectively worthless if you cannot afford to exercise.

5. Refresher grant policy

The offer is the on-hire grant. Most senior engineering roles at established companies also include refresh grants every 1-2 years. The offer letter rarely specifies these.

Ask:

  • "What is the typical refresh grant size at my level here, after year 1 and year 2?"
  • "Is there a clear process for refresher grants tied to performance?"

If the answer is "we do not really do refreshers" — that is a major signal at the senior level. Your effective compensation will drop sharply in years 3-4 as the on-hire grant winds down. Either negotiate a larger on-hire grant to compensate, or expect to renegotiate or leave at the 3-year mark.

What to ask explicitly during the offer call

Print this list, ask each one in order:

  1. Can I see the equity grant terms before signing the offer letter?
  2. What is the dollar value of the equity at the trailing 30-day average share price (or last round price for private)?
  3. What is the vesting schedule and cliff?
  4. (Private only) When was the most recent 409A and is a new one expected before my grant date?
  5. What is the post-termination exercise window?
  6. What is the typical refresh grant cadence at my level here?
  7. Is there a tax-advantaged option election I should be aware of (ISO vs NSO, double-trigger RSUs, 83(b) for early exercise)?

You will not get answers to all 7. You will get answers to most. The pattern of which ones the recruiter answers immediately and which ones they hedge on tells you a lot about how the company actually treats compensation.

Why this matters more in 2026

Two things have shifted:

  • Equity is a larger fraction of senior offers than it was 3 years ago. At several public companies, the equity component is now 40-50% of total comp at L4+. Negotiating the cash and ignoring the equity means negotiating the smaller half of the package.
  • Equity is harder to value. Public-market volatility and slower IPO cycles for private companies mean the stated offer value is more disconnected from realized value than ever. The 5 questions above are how you bridge the gap.

For the cash side of the negotiation, How to Negotiate a Developer Salary (With the Actual Email I Sent) walks through the script that actually moved my last 3 offers. And for the round-2 ("they came back with a counter") moment specifically, What to Say When They Counter Your Counter-Offer has the scripts.

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