Equity Vesting Schedule Calculator

A recruiter tells you the offer includes "$200,000 in equity." In her mind, that's the number you'll earn. In reality, that's the number you might earn if: you stay four full years, the cliff passes, the stock doesn't drop, and nothing weird happens with the company (layoffs, acquisition, down-round). The actual realized value is routinely 40-70% of the headline number for most employees.

I've watched people sign $200k grant offers and walk away with $35k, $90k, or $280k depending on what the company did during their tenure. The volatility is the whole story — and no one at the offer stage is telling you what the realistic distribution of outcomes looks like.

This calculator gives you the math version: what does the grant look like if you stay N years, the stock grows at X%, and the cliff hits when expected? It's a baseline, not a promise. Use it as a floor to reason about everything that could go wrong.

Most startup and public-company equity grants have a one-year cliff. If you leave before your 12-month anniversary, you get zero equity. Not "prorated zero" — literally none. This is intentional: the cliff protects the company from short-tenure employees walking with vested stock.

Consequences:

• If you're recruited away at month 10, you forfeit the entire first-year vest. A $200k/4-year grant at month 10 = $0 vested if the cliff is 12 months. That's $50k of compensation you worked for and don't get. Make the next company buy it out with a sign-on bonus.
• If the company lays you off at month 11, same result — you usually get nothing unless they accelerate vesting (rare for non-executives). Startups do this routinely during downturns.
• If you clear the cliff at month 12, you typically get 25% of the grant at once (the "back-loaded" first-year tranche), then monthly or quarterly vests for the remaining three years.

Negotiate: for experienced hires, ask for cliff acceleration to 6 months, or a cliff-equivalent sign-on bonus to de-risk the first year. Most companies will do one of these if you ask.

Not all equity is the same animal. The flavor determines how you're taxed, what you owe, and what it's actually worth:

• RSUs (Restricted Stock Units). Public-company standard. Each vest is taxed as ordinary income on the day it vests at the market price. You owe income tax even if you don't sell. Common at FAANG, Microsoft, Salesforce, most post-IPO tech.
• ISOs (Incentive Stock Options). Startup standard pre-IPO. You have the right to buy shares at a fixed strike price. If you exercise early and hold, and the company exits, you pay long-term capital gains — much lower tax. But you need cash to exercise, and there's AMT risk.
• NSOs (Non-qualified Stock Options). Less favorable than ISOs. Taxed as ordinary income on exercise at the spread (market price minus strike). Still have the "need cash to exercise" problem.
• PSUs (Performance Stock Units). RSUs that only vest if company or individual metrics hit. Common for executives. Headline number often higher than RSU because achievement is uncertain.

This calculator's math works for RSU-style grants where the grant value represents dollar-denominated equity. For options, you need to adjust: multiply grant share count by (current FMV - strike price) to get the intrinsic value, and treat that as the input.

Raj, a backend engineer, joined a Series C fintech in 2022 at a $185k base + $400k RSU grant over 4 years ($100k/year headline). The company's 409A valuation at grant was $42/share, so 9,524 shares.

What happened: Series D priced flat. Then the 2023 market correction hit. The 409A dropped to $14/share within 18 months. Then a down-round in late 2024 put the 409A at $9/share.

His "vested" equity at month 30 (62.5% vested, 5,953 shares) was worth: 5,953 × $9 = $53,577. The headline said he'd earned $250k of equity by that point. He'd earned about a fifth of that.

He left at month 31. Final realized equity value: $53k + a $19k "sign on" from the next job's buyout = $72k realized. On a $400k headline number over 2.5 years, that's a 28% realization rate.

The lesson: private-company equity is highly correlated with market conditions. If you joined a pre-IPO company in 2021-2022 at a peak valuation, your grant is almost certainly worth less than headline today. Factor it into your tenure planning.

Most companies issue "refresh" grants annually or biennially to keep employees retained past the initial vest. These are typically 25-50% of the original grant value, layered on top of what's still vesting.

The comp cliff problem: if you joined at $200k base + $400k grant ($100k/year vest), your effective comp is $300k. At year 4, the grant fully vests and you're back to $200k base unless refreshes have filled in. If refreshes don't match the original $100k/year rate, your comp effectively drops at the 4-year mark.

Check before accepting: ask the recruiter about refresh grant size and cadence for someone in your level. "What's the typical annual refresh grant value for a Senior Engineer at this company?" If they dodge, it's a yellow flag — refresh culture varies wildly. Some companies refresh generously (Meta, Google). Some refresh poorly (many mid-stage startups). Some don't refresh at all for individual contributors.

After the cliff, vest frequency varies:

• Monthly vesting (most tech companies, post-cliff). 1/48 of grant vests each month for a 4-year grant. Best for employees — you're always accruing.
• Quarterly vesting (some banks, consulting firms). 1/16 per quarter. Slightly worse — three months of risk between vests.
• Annual vesting (rare, some legacy companies). 25% per year. Worst — you risk losing an entire year if you leave early.

When timing a job change, pay attention to vest dates. Leaving two weeks before an annual vest forfeits 25% of your stake. If you're planning a departure, ask your current company when your next vest lands and time around it. Seven-figure grants have been left on the table by people who didn't know they vested two weeks after their resignation date.

If you join an early-stage startup with ISOs or NSOs, you may have the option to early-exercise your grant — buy the shares upfront at the strike price before they vest, and file an 83(b) election to lock in current tax treatment.

Why it matters: if the company's FMV grows during your tenure, you avoid paying income tax on the spread at each vest. Instead, when you eventually sell, you pay long-term capital gains (20% federal vs 37% ordinary). For a pre-seed grant that grows 10x, this can be a $500k+ tax savings.

Why it's risky: you have to spend cash upfront (often $10-50k for early-stage grants, much more for later-stage), AND you have to file the 83(b) within 30 days — miss that deadline and you lose the tax benefit. If the company fails, you lose the exercise money.

Rule of thumb: early-exercise only amounts you can afford to lose entirely. For seed/Series A grants where the total exercise cost is under 3-5% of your net worth, it's often worth it. For later stages where exercise cost is $100k+, talk to a startup tax attorney before pulling the trigger.

Most grants don't vest automatically on acquisition. They require a "double trigger": the company is acquired AND you're let go post-acquisition. If you're retained by the acquirer, your unvested equity typically converts to the new company's equity and continues its original schedule.

Single-trigger (immediate vest on acquisition) is rare and usually reserved for C-suite executives. If you see it in your offer, that's a good sign of seniority-level treatment.

The trap: when a company gets acquired, they often offer you a "retention package" — additional equity grant from the acquirer that vests over 1-2 years post-close. These are usually worth less than your original unvested equity would have been, but you lose the original equity if you don't accept. Always model both scenarios: accept retention and stay 2 years (comp N), or decline, lose unvested, and take a new job elsewhere (comp M). The retention often loses to a good external offer, but you need to know the numbers.