The Equity Grant Negotiation Modeler: Turn a Job Offer's Equity Package Into a Realistic Value Range and Counter-Ask
Why this prompt matters
Candidates routinely accept equity-heavy offers at face value, treating the grant's paper value as if it were cash, without modeling that most startup equity at this stage realizes far below the headline number. The reverse mistake is just as costly: assuming equity is worthless and walking away from an offer that was actually competitive once properly valued. Either error compounds for years, since total compensation at the next job is frequently anchored to what you accepted this time.
What we use it for
A software engineer receives a job offer from a Series C startup — $150,000 base plus 20,000 RSUs at a $4.00 latest 409A valuation, 4-year vest with a 1-year cliff — and has a competing offer elsewhere at $175,000 base with no equity. They need to decide, within a few days, whether the equity story justifies the lower cash offer, and if not, what specifically to ask for instead.
Prompt
Act as a compensation analyst and negotiation coach who specializes in evaluating equity-heavy job offers. You help candidates see past the headline number on an offer letter and negotiate from an informed position. Context: - The offer: [BASE SALARY, EQUITY TYPE (RSU/ISO/NSO), NUMBER OF UNITS OR PERCENTAGE, STRIKE PRICE OR LATEST VALUATION, VESTING SCHEDULE] - Company stage and context: [FUNDING STAGE, E.G. SERIES B, TIME SINCE LAST ROUND, ANY KNOWN GROWTH OR RISK SIGNALS] - Your alternative: [COMPETING OFFER OR CURRENT COMPENSATION, IF ANY, FOR COMPARISON] - Your situation: [RISK TOLERANCE, NEED FOR CASH LIQUIDITY NOW VS. LATER, HOW LONG YOU REALISTICALLY EXPECT TO STAY] Task: 1. Build three valuation scenarios for the equity — downside, base case, and upside — using explicit, stage-appropriate assumptions about exit likelihood and valuation multiples. State every assumption out loud; do not present a single number as if it were certain. 2. Convert each scenario into an annualized expected value across the vesting period, and compare that to the cash-equivalent value of [YOUR ALTERNATIVE]. 3. Identify the single highest-leverage lever to negotiate — more equity, a shorter cliff, a signing bonus, or higher base — based on where this specific offer is weakest relative to [YOUR ALTERNATIVE] and your stated risk tolerance. 4. Draft the exact counter-ask message to send back to the recruiter or hiring manager. Constraints: - Do not manufacture false precision. Label every dollar estimate as resting on a stated assumption, not a fact. - Recommend negotiating only one or two levers, not everything at once — a counter that asks for five things gets none of them. - Do not recommend accepting or rejecting the offer; your job is to inform the decision, not make it. - Keep the counter-ask message itself under [WORD LIMIT, E.G. 150] words. Output Format: - A three-row scenario table (downside / base / upside) with dollar estimates and the assumption behind each. - One paragraph naming the single biggest lever to negotiate and why it's the highest-leverage ask given the numbers above. - The counter-ask message, ready to send.
Result
Scenario table (20,000 RSUs, $4.00 current share price per latest 409A, 4-year vest, 1-year cliff):
- Downside (no exit within vesting window, 409A stays flat or declines — historically the modal outcome for Series C companies that haven't raised again in 18+ months): $0–$20,000 realized value. Assumption: roughly 60% of Series C startups at this funding age either stall, get acquired below the last preferred price, or wind down before a liquidity event. - Base case (modest markup at next round, partial liquidity via tender offer in year 3): ~$60,000 realized value over 4 years ($15,000/year equivalent). Assumption: a 1.5x markup on the current valuation, consistent with typical Series C-to-D markups in a stable market. - Upside (successful Series D or acquisition at a 4x markup): ~$160,000 realized value over 4 years. Assumption: a top-quartile outcome, which by definition applies to a minority of companies at this stage.
Comparing against your competing offer of $175,000 base with no equity: your current offer's $150,000 base plus equity only beats the competing offer in the upside scenario. In the downside and base cases, you're accepting $15,000–$25,000 less per year in exchange for equity that may be worth little or nothing.
Recommendation: The highest-leverage lever here isn't asking for more equity — you already have a meaningful grant relative to level. It's closing the base salary gap. A $15,000 base increase would make the offer competitive even in the base-case equity scenario, without asking the company to dilute further or restructure the vesting you've already negotiated.
Counter-ask message:
"Thank you for the offer — I'm excited about the role. I have a competing offer at $175,000 base with no equity. Given that, I'd like to ask if there's room to bring the base salary to $165,000. I'm not asking to change the equity grant or vesting structure, just to close the cash gap given the alternative I'm weighing. Happy to discuss what's possible this week.
Most equity negotiation advice collapses into one of two bad defaults: treat the paper value of the grant as real money, or dismiss it entirely as a lottery ticket not worth factoring in. Both mistakes come from skipping the actual math. This prompt forces three explicit scenarios — downside, base case, and upside — each anchored to a stated assumption about the company's stage and realistic exit outcomes, so the candidate is comparing an honest range against their alternative, not a single optimistic or pessimistic guess.
The second half of the prompt is just as deliberate: it forces the output to name exactly one or two negotiation levers, not a wishlist. Compensation negotiations that ask for everything at once — more equity, faster vesting, higher base, a signing bonus — tend to get nothing, because the counterparty has no clear signal about what actually matters to the candidate. Naming the single highest-leverage ask, grounded in where the specific offer is weakest, gets a real answer instead of a stall.