← Insights·Compensation

Evaluating an Executive Job Offer: Cash First, Then Equity

Separate salary, bonus and equity by their payment conditions before you compare offers or negotiate.

By Ken Gavranovic · October 29, 2026

The new offer looks like a raise. Most of the advantage sits in the target bonus and equity.

That may be a good deal. But the total combines a salary rate, conditional cash and an equity award that may take years to become spendable money. Correct addition doesn't make those dollars interchangeable.

Before you decide to accept, negotiate or stay, ask what each part has to survive before you can plan around it. I'd establish the cash terms first, then follow each award through vesting and payment or sale. Cash-first doesn't mean choosing the most cash. It means understanding the risk you're taking with the rest.

Start with the cash terms

Base salary is an annual rate while you're employed, not a guarantee of multiyear employment. Model it over the same dates in both packages.

An annual bonus target is conditional cash. It may be expressed as a percentage of base and depend on company results, individual results or both. Ask how the payout is calculated, what discretion the employer retains, when you're first eligible and what happens if you leave before payment. Don't put the target amount in the guaranteed column unless the written terms actually guarantee it.

Sign-on money has conditions too. Establish when it arrives and what could require you to repay it. Keep a one-time payment out of your recurring annual pay.

If moving would cost you a bonus or unvested equity, a sign-on is one possible replacement to request. First establish what you'd actually forfeit under your current plan.

Count that loss once. In a side-by-side comparison over the same period, put the bonus you'd receive by staying only in the stay column, and the replacement sign-on only in the move column. That difference already reflects the lost bonus. Don't subtract it again as a separate moving cost. Keep payment dates and repayment conditions visible: replacing the face amount doesn't necessarily replace the timing or security.

Check material differences in retirement contributions, health coverage and other benefits separately. They can change the comparison without showing up in the headline cash number.

Follow the equity past the vesting date

Start by establishing what you're being offered: options, shares, restricted stock units or another instrument. Ask how the employer calculated the dollar figure, what quantity it represents and what approvals remain. A grant-date valuation is not a forecast of sale proceeds.

Vesting determines your entitlement under the award's conditions. Some awards depend on continued service; others add performance requirements. If a portion requires an investor-return hurdle to be met at a sale, completing the service period alone won't earn that portion.

Then separate vesting from liquidity. When are shares or cash actually delivered? For options, what would exercising cost, and by when would you have to act? When could you sell, what restrictions apply and whose approval would you need?

Shares you can sell today deserve different treatment from an award waiting for a private-company exit. If the only route to cash presented to you is a future sale of the company, test a later sale too, including the possibility of no payout. Don't turn management's hoped-for exit year into your household's payment date.

Departure terms matter just as much. What happens to vested and unvested awards if you resign or are terminated without cause? Does the option exercise window change after departure? What happens on a sale or change in control?

Ask for the plan and award agreement, not only the offer's summary. Where a term is missing, mark it unknown. Not zero, not the optimistic version. Unknown.

Your current equity flow can mislead you

Run the same review on your current package, especially if several years of grants overlap. The amount vesting this year may be a temporary peak.

Consider an invented example. You have four overlapping stock grants, each worth $400,000 when granted and each vesting in four equal annual installments. Three were granted at today's share price. The oldest was granted at one-quarter of that price.

If today's price holds through this year's vest dates and you meet the vesting conditions, the three newer grants each release $100,000 of stock. The old one releases $400,000. Total: $700,000 before tax.

When the old grant finishes, suppose a new $400,000 grant at today's price replaces it on the same vesting schedule. At an unchanged share price, annual vesting value falls to $400,000. One unusually appreciated grant has finished paying out. These are illustrative values, not market benchmarks or forecasts.

A promotion or retention award could reduce or eliminate that step-down. Ask about future grants, but keep them separate from awards already made. An expected refresher is not an awarded grant.

This matters when you're comparing a new offer with staying. Last year's unusually valuable vesting isn't necessarily what you're leaving behind next year.

Test the trade you're willing to make

Equity can be the best part of a package. If the business succeeds and the award's terms let you participate in that success, the upside may outweigh a lower salary. Someone who can cover their needs without an early equity sale may reasonably choose that trade.

Before trading salary for early-stage equity, ask whether you believe in the product, market and team, and whether you can afford a disappointing result. Those are different questions. Believing harder doesn't make a grant worth more.

I'd put both packages on a simple schedule, with each award separate. Cover the vesting period and any later liquidity event you are assuming, rather than stopping automatically at year four. Keep assumed raises, discretionary refreshers and exit proceeds visibly separate from agreed terms.

Then change the assumptions that could affect your choice. What if no additional refresher arrives? What if the private-company sale is delayed, or you leave before an important vesting date? Also consider a successful outcome with meaningful upside. The purpose isn't to make every scenario pessimistic. It's to see which assumptions your decision depends on.

A completed schedule won't tell you what the business will be worth or how likely a payout is. It can tell you which unanswered question matters enough to bring back to the employer.

Negotiate the condition that changes your answer

Suppose the offer includes a target bonus, but you learn that your start date makes you ineligible for the first performance year. Increasing the target won't fill that first-year gap. A sign-on payment or a written first-year bonus guarantee might, depending on its amount, payment date and conditions.

Or suppose the decisive problem is waiting for a private-company sale. A larger award under the same liquidity terms doesn't bring the cash forward. If you need more recurring cash to make the move workable, ask about base salary.

Bring a coordinated request built around the few terms that could change your decision. Explain the gap you're trying to close and the specific change you're asking for. For a pay increase, support the amount with the role's scope, relevant market evidence and the contribution you can credibly make.

Before quoting a benchmark, check the actual function and responsibility, geography, industry, company size, stage and ownership. Read the underlying report's date, population, sample size and statistic. A median and an average are different measures. So are base salary, cash compensation and total compensation including equity. Check whether the figures describe targets, grant values or amounts actually received. A broad manager survey is a lead, not automatically an executive benchmark.

Use that evidence to establish a range for this role rather than simply adding a percentage to your current pay. Compare equivalent components, then consider the package as a whole with its conditions intact.

Coordinated doesn't mean one shot. If an answer changes a material assumption, a follow-up is warranted. Resolve consequential terms before accepting instead of reopening the bargain afterward because you didn't review them.

The employer may have a fixed pay band or an equity plan it won't change. Other terms may be available, but don't assume they will move. An earlier salary review can be useful; even with written criteria, it isn't a promised raise.

Get agreed changes into the documents that govern payment, and get qualified legal or tax advice in your jurisdiction on consequential terms before signing. If a decisive term remains missing, ask for more time or decide whether you can accept the unresolved risk. The company can say no. So can you.

A big interview or an offer on the table?

See how I can help you prepare.

Keep reading

Work with KenMore insights