Most candidates negotiate base salary hard, then sign the equity grant exactly as it was written. That’s the half of the offer they understand least, and at senior tech levels it’s the line with the widest range of outcomes.
Equity negotiation isn’t about knowing finance or being greedy. It comes down to six questions you ask before you sign: what the grant is actually worth, how you keep it, and what happens if you leave. Most candidates ask none of them, largely because nobody ever told them the stock was negotiable in the first place.
Why equity negotiation gets skipped
Base pay is legible. It’s one number, it has a market range, and you can look up what your level pays in about four minutes. Equity arrives as a share count bolted to a valuation that sounds invented. So candidates do the rational thing with a number they can’t read – they nod, file it under “upside,” and go back to arguing about base.
That instinct isn’t stupid. It’s just expensive. Across 250+ placed clients, the ones who negotiate see roughly +$26K in total comp, and most of that lands in base or sign-on, because those are the levers people know how to pull. Meanwhile the stock sits untouched.
Untouched compounds, though. An extra $5K in base is closer to $50K over five years once raises stack on top of it. Equity behaves the same way, except the multiplier runs bigger and the variance runs wider. In my experience, pay disparity almost always traces back to two prior negotiations where someone accepted the first number handed to them. The grant is where that habit likes to hide.
The 6 questions that drive an equity negotiation
Ask these before you counter. Information first, then the ask – because you can’t negotiate a number you’re unable to evaluate.
1. What percentage of the company does this grant represent?
“40,000 shares” tells you nothing. Forty thousand out of how many? A grant is a fraction, and they’ve handed you the numerator while keeping the denominator. So ask for the percentage of fully diluted shares outstanding. If the recruiter won’t say, that’s data too.
2. What’s the strike price, and what’s the current 409A valuation?
At a private company, options give you the right to buy at the strike price. When strike equals today’s 409A valuation, your grant is worth exactly zero on the day you sign. You’re buying future upside, not present value. That’s fine, as long as you know that’s the trade you’re making.
3. What’s the vesting schedule, and where’s the cliff?
Four years with a one-year cliff is the default. Back-loaded schedules aren’t. Some companies vest 5% in year one and 40% in year four, which means the headline number and the number you’d actually hold after two years are wildly different. Therefore: run the math on the horizon you’d realistically stay, not the horizon on the offer letter.
4. What’s the refresh policy at my level?
Here’s the failure mode nobody warns you about: your initial grant vests out in year four, and your comp quietly falls off a cliff while your title stays the same. Refresh grants are what prevent that. Ask what people at your level typically get, and ask when the refresh cycle runs. A company without a real answer has told you something about how it operates.
5. How long do I have to exercise if I leave?
The standard window is 90 days after you walk out the door. For senior people at a company that’s grown, exercising can mean a six-figure check plus a tax bill on paper gains you can’t sell. That’s not a benefit, it’s a set of handcuffs. Some companies offer extended windows of seven to ten years. Almost nobody asks, so almost nobody gets it.
6. What happened in the last round, and what’s the preference stack?
Investors usually hold preferred stock, which gets paid before your common stock does. Consequently, a company can sell for $1B while your slice pays out far less than the arithmetic suggests. You don’t need the full cap table. You need to know whether preferences stack ahead of you, and roughly how much.
RSUs are simpler, not automatic
At a public company, restricted stock units are close to cash on a delay, plus a tax event. There are fewer knobs to turn – no strike price, no 409A, no preference stack. Still, the grant size and the vesting schedule remain negotiable, and the same refresh question applies. Simpler doesn’t mean settled.
How to ask without giving up ground
Once you have the answers, the ask itself follows the same rules as the rest of the offer. Nothing strengthens it like a competing offer, but you can hold ground without one. Anchor on total compensation and say you’re flexible on the mix: “This is the total comp I’m targeting, and I’m flexible on how we get there.” Then stay quiet about your fallback. If a sign-on bonus is the concession you expect to land on, don’t name it first, because they’ll grab it and stop moving on everything else. Let them offer the bridge.
Strip the deference out of the email, too. “I wanted to ask” is you requesting permission to negotiate. “I’m genuinely excited to join” tells them you’ve already decided, so why would they pay more? As Deepak Malhotra argues in HBR, likability and firmness aren’t opposites – you can be warm and still hold the line. They made you an offer for your services. You’re providing something in return.
One more sequencing note: keep the conversation with the person who owns the decision. When a recruiter punts you to someone else on equity specifics, that’s usually a signal about how much room exists, not about who has the spreadsheet.
Common equity negotiation questions
Is equity actually negotiable, or is it fixed by band? It’s negotiable, particularly at senior levels and at startups. Bands exist, but grants vary inside a band, and refresh timing is a judgment call rather than a formula.
Should I push for more equity or more base? Base is certain and compounds through every future raise. Equity is variable and depends on an exit you don’t control. If you need the money in the next three years, weight base. If you’re betting on the company and you’ve done the math above, weight equity.
What if the recruiter won’t answer the percentage or 409A question? Ask once more, in writing, politely. If the answer stays vague, treat the grant as worth close to zero when you evaluate the offer. Opacity is an answer.
Do these questions apply to a public company? Four of them do: percentage, vesting, refresh, and grant size. Strike price and preference stack are private-company concerns.
What to do next
If you want to know which part of your search is actually leaking, take the RHINO quiz. Five minutes, no email required.
If the offer stage is the part you want to get right, read How to Negotiate a Job Offer Without Leaving Money Behind next – it covers the levers beyond the stock grant.
If you have an offer on the table right now and you’d rather have someone hold the line where your own nerves won’t, book a free strategy call.