Equity Compensation Planning

RSU, ESPP, and Stock Option Planning for Tech Professionals.

Your equity pays you in pieces, on a schedule, with tax rules that change by type. We help you see the whole picture and plan around it, with your CPA.

Who this is for

This page is for software engineers, engineering and product managers, directors, and leaders at public tech companies and pre-IPO startups. Your pay probably comes in several forms: salary, bonus, and equity compensation (company stock, or the right to buy it, given as part of your pay).

Each form is taxed differently, and the pieces rarely fit together on their own. Our job is to put them into one coordinated plan with the rest of your finances. Most of our clients earn $200,000 or more.

RSUs: shares that arrive on a schedule

RSUs (restricted stock units) are company shares you receive on a vesting schedule. Vesting is the date a share becomes yours.

When RSUs vest, their value is generally taxed as ordinary income, like salary, and appears on your W-2. Your company usually withholds tax by keeping some of the shares or taking cash. That withholding often uses a flat rate that can be lower than your actual tax bracket, which is one reason people owe more when they file.

What we help you work through

  • How much tax this year's vests add, and whether you've set enough aside
  • Whether to make an estimated tax payment, which you would confirm with your CPA
  • How vested shares fit your goals, rather than just piling up
  • How upcoming vests line up with cash needs such as a home or college

ESPP: a discounted way to buy your employer's stock

An ESPP (employee stock purchase plan) lets you buy company shares through payroll deductions, often at a discount.

How long you hold the shares after you buy them changes how the discount and any gain are taxed. The rules are detailed, so we model the choices with your CPA before you decide.

What we help you work through

  • How much to contribute, given your other goals
  • How your plan's discount and holding periods work
  • Whether ESPP shares add to a company-stock concentration you already have

Stock options: ISOs and NSOs

Stock options give you the right to buy company shares at a set price, called the strike price. ISOs (incentive stock options) and NSOs (non-qualified stock options) are the two main types. Buying the shares is called exercising.

NSOs are generally taxed as ordinary income on the gain when you exercise. ISOs are not taxed as regular income at exercise, but the gain can trigger the AMT (alternative minimum tax), a parallel tax calculation that affects some high earners. Spreading exercises across tax years can change the result.

At a pre-IPO startup you may also hear about two other terms. An 83(b) election is a filing that lets you choose to be taxed on restricted stock when you receive it, rather than as it vests. The deadline is 30 days from the grant, so ask early. A tender offer is when the company or outside investors offer to buy shares from employees before an IPO.

What we help you work through

  • When an exercise could make sense, and how much cash it would take
  • How much AMT an exercise might create
  • What a tender offer is worth to you after taxes, and the trade-offs
  • What happens to your options if you leave (many plans allow about 90 days, so check your grant agreement)

Want the deeper tax detail? Read RSUs, ISOs, and NQSOs: The Difference That Actually Matters at Tax Time.

Concentrated stock: when one company is too much

Concentrated stock means a large share of your net worth sits in one company's stock.

If you work there, the same company pays your salary, drives your bonus, and sets the value of your shares. A rough stretch for the company can hit all three at once. That is a risk to understand, and not a reason to act on a hunch.

We do not tell you to buy, sell, or hold any specific stock. We help you decide how much of your net worth you're comfortable having tied to one company, then map out the ways to get there and the tax cost of each. Common approaches include setting a target percentage, selling shares on a schedule as they vest, or giving appreciated shares to charity. Each has trade-offs.

This work sits alongside our investment management, where we build the rest of your portfolio around your goals.

Job offers and layoffs

Weighing a job offer

Compare offers on total pay, not just salary. Private company equity can be hard to sell, so its value is less certain than shares of a public company.

  • Base pay and bonus
  • The size and vesting schedule of any RSU grant, including a cliff (a waiting period before the first shares vest)
  • For options, the strike price and how long you have to exercise after you leave
  • Benefits, 401(k) match, and remote or relocation terms

Planning for a layoff

Unvested RSUs and options are usually forfeited when you leave, and vested options often have a limited window to exercise. Severance (pay your employer gives when your job ends) can change your taxes for the year. A plan made before you need it makes a hard moment easier.

  • How many months of expenses your cash and severance would cover
  • What happens to unvested shares and options under your grant agreement
  • Your health coverage options after your job ends
  • Which accounts to draw on first if you need cash

Saving more from a high income

A backdoor Roth is a way to put money into a Roth IRA when your income is too high to contribute directly. A mega backdoor Roth uses after-tax contributions to a 401(k), if your plan allows them, and moves that money into Roth savings. Whether either one is available or sensible depends on your plan and your tax picture.

How we work with your CPA

We do not prepare tax returns or replace your CPA. We build the plan, estimate the tax effect of equity events, and, with your permission, share those numbers with your CPA so the two of us work from the same page. Your CPA confirms the tax treatment and files your return.

Keep going

This page is for general education only. It is not personalized investment, tax, or legal advice. Tax rules change and depend on your situation, so coordinate with your CPA before acting. See our disclosures.

Have a vest or exercise coming up?

Start with the checklist, or talk it through on a free 30-minute call.