Equity for Chiefs of Staff: Understanding Startup Equity

Comp & Careers

May 21

Takeaway: For a startup chief of staff, equity can be a meaningful part of the package, but it is speculative and cannot be judged from a headline percentage alone. Learn the mechanics, gather the ownership and economic terms, and never confuse a large-sounding grant with realized money.

Equity is common in startup Chief of Staff packages, but it's not universal. In the small, UK-heavy Chief of Staff Collective 2025 survey (n=63), 54% held equity. It can be meaningful upside. It can also be close to worthless, and the difference usually comes down to details the candidate never asked about. This guide covers the mechanics you need to evaluate an equity offer with clear eyes. None of it is tax or financial advice; for anything with real money on the line, talk to a professional.

The three things you might be offered

Startup equity comes in a few forms, and they behave differently.

Incentive Stock Options (ISOs) give you the right to buy company shares at a fixed price, called the strike price, at some point in the future. ISOs are available only to employees and can carry favorable tax treatment if you meet the holding-period rules, though exercising them can still trigger the alternative minimum tax, so the tax picture isn't automatically simple (Carta). They are the most common form for early employees at a startup.

Non-Qualified Stock Options (NSOs) also give you the right to buy at a strike price, but without the special tax status of ISOs, and they can be granted to contractors and advisors, not just employees. With NSOs you generally owe ordinary income tax on the difference between the strike price and the fair market value at the moment you exercise.

Restricted Stock Units (RSUs) are a promise of actual shares, not the right to buy them, delivered when they settle. RSUs are more common at later-stage and public companies, and are taxed as ordinary income when they settle, based on the value at that time. At private companies RSUs often carry a double trigger, converting to shares only when both a time-based schedule and a liquidity event such as an acquisition or IPO are met, so they may not simply vest or become taxable on a set date. If you are joining an early startup and someone offers you RSUs, that is a signal about stage.

The practical difference: options are only worth something if the company's value rises above your strike price, while RSUs have value as long as the stock is worth anything at all. Options carry more upside and more risk.

Strike price and the 409A valuation

If you are granted options, the single most important number after the grant size is the strike price, because it is what you will pay per share to exercise. That price is set by the company's most recent 409A valuation, an independent appraisal of the fair market value of a private company's common stock (Carta). Under Section 409A, options must be struck at no less than fair market value on the grant date, and a 409A appraisal is how a company establishes that value and protects both itself and you from the tax penalties of underpricing.

Two implications matter for you. First, a lower strike price is better, because your gain is the difference between the strike price and what the shares eventually sell for. Joining earlier usually means a lower strike. Second, the 409A value is not the same as the price investors pay. Investors buy preferred stock, which carries protections; employees get common stock, which is worth less. When a recruiter quotes a headline value for your grant based on the last funding round's price, that headline number can overstate what your common shares are worth today.

Vesting and the one-year cliff

You do not get your equity all at once. It vests over time, and the most common schedule at startups is four years with a one-year cliff. That means you typically earn nothing if you leave in the first twelve months. At the one-year mark, 25 percent commonly vests in a single chunk, and the remainder vests in monthly or quarterly increments over the following three years (Holloway).

The cliff has a real consequence for chiefs of staff specifically. The role has high early-attrition risk, because it depends so heavily on fit with one person. If that fit is wrong and you leave at month ten, you walk away with zero equity, no matter how well you performed. That is not a reason to avoid the role. It is a reason to weigh the equity portion of an early offer realistically rather than as guaranteed compensation, and to pay attention to the relationship before you sign.

Why there is no reliable Chief of Staff grant benchmark

This is the part everyone wants a number for, and it is the part to be most careful with. Equity grants vary enormously by company stage, role scope, dilution, option type, and candidate leverage. There is no robust, stage-adjusted public benchmark for Chief of Staff equity specifically.

Published startup-equity tools can still provide scenario context. Index Ventures models VP grants around 0.3 to 0.8 percent of fully diluted equity at Series A and roughly 0.2 to 0.7 percent at Series B, with a full C-suite hire nearer 1 percent at Series A and B (Index Ventures). Those are employer planning scenarios built from startup grants, not Chief of Staff benchmarks. Holloway's guide illustrates the same pattern, equity dropping sharply with hire timing and funding stage, though its underlying numbers draw on older market data and are best read as directional (Holloway).

Don't automatically place a Chief of Staff at or below a generic VP band. "Chief of Staff" spans a junior coordinator through a near-executive running the company operating cadence, and no validated source maps those scopes cleanly onto VP grant data. Use generic ranges only to understand possible scenarios, then evaluate the actual grant from its ownership, economics, and terms.

The questions to ask before you sign

An equity number means little without context. Before you accept, ask the company:

How many total fully diluted shares are outstanding, so you can turn your grant into an actual percentage rather than a raw share count?
What percentage of the company would the grant represent on a fully diluted basis today?
What is the current strike price and the date of the last 409A valuation?
What was the price and post-money valuation of the most recent funding round?
What is the vesting schedule and cliff?
ISOs, NSOs, or RSUs?
What is the post-termination exercise window, meaning how long you have to buy your vested options if you leave?
How have recent financing rounds diluted employees, and does the company offer refresh grants?
What does the liquidation-preference stack look like ahead of common shares, and do any investors hold participating preferred, so you can see who gets paid first in a sale?
What happens to the grant if the company is acquired or your role ends after a change in control?

A company should be able to share enough for you to understand the award. Some cap-table details are legitimately confidential, but a refusal to disclose your ownership percentage, strike price, vesting, or the actual grant documents is a material limitation you should weigh.

Keep it in perspective

Equity at a startup is speculative, illiquid upside, not a paycheck. The sober way to evaluate an offer is to make sure the cash compensation works on its own and run a zero-value equity case. A grant that looks enormous on paper can be worth nothing if the company doesn't succeed, if liquidation preferences absorb the proceeds, if your strike price is high, or if you leave before the cliff. Understanding the mechanics lets you distinguish a transparent grant from one engineered to sound impressive, even though no checklist can guarantee an eventual outcome.

FAQ

What is the difference between ISOs, NSOs, and RSUs? ISOs and NSOs are options, the right to buy shares at a set strike price; ISOs can carry favorable tax treatment and are employee-only, though exercising them can trigger the alternative minimum tax, while NSOs can go to contractors and are taxed as ordinary income at exercise. RSUs are outright shares delivered at settlement, common at later-stage and public companies, and taxed as income when they settle (Carta).

What does a one-year cliff mean? On a standard four-year schedule with a one-year cliff, you typically earn no equity if you leave within the first twelve months. At one year, 25 percent commonly vests at once, and the rest vests gradually over the remaining three years (Holloway).

How much equity should a chief of staff get? There is no reliable CoS-specific benchmark. Generic VP figures from tools such as Index Ventures can illustrate scenarios, but they don't establish what a Chief of Staff should receive. Judge the actual grant from fully diluted ownership, strike and 409A information, funding terms, vesting, exercise window, dilution, liquidation preferences, and liquidity.

What is a strike price and why does it matter? The strike price is what you pay per share to exercise an option, set by the company's 409A valuation. A lower strike means a larger potential gain, since your profit is the difference between the strike and the eventual sale price (Carta).

Is startup equity usually worth a lot? It can be worth a great deal or nothing. It's illiquid and can stay that way for years, and many companies never reach an exit that makes common shares valuable. Evaluate an offer as if the equity might be zero, make sure the cash works on its own, and treat the equity as upside rather than guaranteed pay.

For a deeper walk-through, join The Brief, our free newsletter for exec-ops professionals, and get our startup-equity evaluation worksheet, a one-page checklist of the numbers and questions to work through before you accept an offer. It is an education tool, not financial advice.

Adrienne Gaughan