How to Negotiate Equity and Stock Options in a Job Offer

Equity is the part of a US offer most people either ignore because the mechanics feel opaque, or over-trust because a big headline number sounds impressive. Both are mistakes, and the two situations — RSUs at a public company, options at a startup — need almost entirely different evaluations. Treating them the same is how people end up either underselling a strong RSU package or overvaluing options that are worth a lot less than the headline number implies.

RSUs at a public company: the grant size is only part of the story

Restricted stock units at a public company are close to cash — they have a real, daily market price, and once vested they're yours to sell. That makes them easier to evaluate than startup options, but people still leave value on the table by fixating only on the headline grant number.

What actually matters as much as the size of the grant:

• The vesting schedule and cliff. A grant "worth" $200k over four years with a standard 25%/year vest is very different from one back-loaded so more vests in years 3-4 than year 1 — the second is worth less to you if you might leave in year two, and worth more if you're planning to stay long-term. Ask for the exact schedule, not just the total.
• Refresh grants. Public-company comp increasingly comes through annual refresh grants on top of the initial sign-on grant. Ask what a typical refresh looks like for someone performing well at your level — the initial grant is a one-time number, refreshes are the ongoing story.
• Stock price assumptions. If the offer letter quotes equity value using a stock price from months ago, or an internally optimistic number, the real value moves with the actual market price by the time you vest. Don't treat the headline dollar figure as fixed.

A reasonable counter, similar to countering base salary, is asking for roughly 10-25% more shares than the initial offer, especially if you have a competing offer or a strong case based on level and market comps — the mechanism is the same as countering a base number, just denominated in shares instead of dollars.

Startup options: ownership percentage, not share count

This is where most candidates get misled, not through bad faith but through a genuinely confusing structure. A startup offer that says "10,000 options" tells you almost nothing on its own. What matters is what fraction of the company that represents, and what it costs you to actually own it.

Ask for, specifically:

• The fully diluted share count — the total number of shares outstanding across all classes, including everyone else's options and any reserved-but-ungranted pool. Your 10,000 options against a company with 10 million fully diluted shares is a meaningfully different offer than the same 10,000 against 100 million. Ownership percentage is the number that matters, not the raw share count, and you can't calculate it without this figure.
• The strike price, and how it compares to the last 409A valuation. The strike price is what you'll pay per share to exercise; the 409A is an independent appraisal of the company's common stock value. A strike price close to the current 409A means less built-in gap for you to profit from immediately; a wide gap between them is more favorable, on paper, assuming the company's value actually grows from here.
• The vesting schedule and what happens if you leave. Most startups use a four-year vest with a one-year cliff — nothing vests until you've been there a year, then it vests monthly or quarterly after that. Also ask about the post-termination exercise window: some companies give you only 90 days after leaving to exercise vested options and pay the strike price out of pocket, which can be a real financial squeeze; others extend that window, which is a meaningfully better term even if the share count is identical.

A company that's cagey about the fully diluted share count or the 409A when you ask directly is worth noting — it's a normal, standard question at any startup with a real cap table, and reluctance to answer it plainly is itself information.

Negotiating the counter

The same 10-25% framing applies to startup options as to RSUs — asking for more shares than the initial offer, particularly with a competing offer or a leveled market comp to point to, is a normal and expected ask. It's easier to move than base salary at an early startup for the same reason a signing bonus is easy to move at a larger company: it doesn't touch the immediate cash burn rate the way a base increase does.

This is exactly the kind of lever worth raising as part of negotiating the full offer, not in isolation — equity, base, and signing bonus often trade off against each other, and knowing which one the company has more room to move on before you counter changes how you sequence the ask.

Rehearsing the conversation

None of the above is a conversation-practice problem — it's a spreadsheet problem, and no amount of rehearsal replaces actually running the fully diluted math or checking a 409A. Where practice does help is the live moment: asking a recruiter directly for the fully diluted share count without it sounding like an accusation, or holding your counter when they say "that's just what we offer at this level" and you need to ask a clarifying follow-up instead of folding.

Prepair's salary negotiation practice covers that live conversation skill — Cam plays your recruiter or hiring manager, you practice asking the pointed questions and countering in a turn-based exchange, and you get a scored readout afterward. It's part of the Pro plan, text or voice. It is honestly not the tool for the math itself — get the fully diluted numbers and the 409A in writing and run the actual ownership percentage yourself, or with someone who knows cap tables. What it's for is not freezing up when you ask a startup for their fully diluted share count and they push back on giving it to you.