Build it
Your equity is a plan, not a bonus
Vest dates arrive whether or not anyone has thought about them. The work is deciding, ahead of time, what you sell, what you hold, and what the tax bill will be.
In one paragraph
Equity compensation planning is the work of deciding what to do with company stock before it vests or expires. It covers withholding, sale timing, concentration limits, and which tax treatment applies to each grant type, so RSUs, options, and ESPP shares are handled on a schedule instead of a reaction.
The problem
The part nobody warned you about
Your grant letter explains what you were given. It says nothing about what to do next. So the default happens: shares vest, your employer withholds a flat 22% for federal tax, and the position sits in the same account it landed in.
Two problems compound from there. If your household income puts you in the 32% or 37% bracket, that 22% withholding is short, and the gap surfaces as a bill at filing or as an underpayment penalty. Meanwhile your net worth quietly concentrates in the same company that already pays your salary.
Options add a clock. Incentive stock options can trigger alternative minimum tax in the year you exercise, even with no shares sold. Non-qualified options create ordinary income at exercise. Both expire, and both are easy to leave until the notice arrives.
What we actually do
The work, item by item
- 01
Map every grant on one page
Grant type, grant date, vest schedule, strike price, expiration. Most people have this in three portals and one PDF. We put it in one view so decisions stop being guesses.
- 02
Close the withholding gap before filing
We estimate what each vest actually costs at your marginal rate, then decide whether to raise withholding, make an estimated payment, or sell shares to cover it.
- 03
Set a concentration limit you can live with
You pick the percentage of net worth you are willing to hold in employer stock. We build the sell schedule that keeps you there, so it stops being an emotional call each quarter.
- 04
Sequence exercises around the tax year
Which options to exercise, in what order, and in which year. For ISOs that means watching the AMT line; for NSOs it means managing the ordinary income you are adding on top of salary and bonus.
- 05
Use the sale to fund something real
Diversification is not the goal by itself. Proceeds go toward the things you told us matter: the tax bill, the house, the education fund, the point where work becomes optional.
- 06
Loop in your CPA before the year closes
Most equity mistakes are timing mistakes, and timing decisions belong to December, not April. We bring your accountant into the conversation while it can still change the outcome.
An example
What this looks like in practice
A director at a medical device company has 1,800 shares vesting over the next twelve months and about 40% of her net worth already in company stock. She has never sold a share because the stock has been good to her.
We start with the tax number, because it is the one with a deadline. Then we agree on a ceiling for employer stock and set a quarterly sale schedule that walks her down to it over two years rather than all at once. The proceeds have jobs assigned before they arrive.
Nothing here required a market call. It required a decision made on a calm Tuesday instead of the week of a vest.
A composite illustration, not a specific client. Your situation and results will differ.
Free tool
Vesting this year? Find the tax bill nobody warned you about.
Employers commonly withhold federal tax on vesting RSUs at 22%. Plenty of the people we work with sit in the 32% or 37% bracket, and that difference shows up as a bill at filing. Five inputs and about twenty seconds gives you the number.
- Shares vesting
- 1,200
- Value at vest
- $180,000
- Withheld at 22%
- $39,600
- Owed at 35%
- $63,000
- Gap to cover
- $23,400
Straight answers
Equity compensation: common questions
Employers commonly withhold federal tax on vesting RSUs at the 22% supplemental wage rate. If your total household income puts you in the 32% or 37% bracket, that withholding falls short of what you owe, and the difference appears when you file. State tax and the additional Medicare tax can widen the gap further. The fix is knowing the number early enough to adjust withholding or make an estimated payment.
Selling at vest is worth considering because RSUs are taxed as ordinary income on the vest date regardless of what you do next, so holding is a separate investment decision from the compensation itself. Ask yourself whether you would buy that stock with a cash bonus of the same size. The right answer depends on how concentrated you already are and what the proceeds would fund, which is exactly what we work through together.
Incentive stock options can receive favorable long-term capital gains treatment if you meet holding requirements, but exercising them may create alternative minimum tax exposure in the year of exercise. Non-qualified stock options create ordinary income on the spread at exercise, withheld like wages. The planning differs enough that the two should never be handled with the same default.
There is no universal number, and anyone who gives you one without knowing your situation is guessing. The useful frame is that your salary, bonus, equity, and often your health insurance already depend on one employer. Concentration in the stock stacks another layer of the same risk. Many people land somewhere between 10% and 20% of net worth once they see it laid out.
Related
These usually come up alongside it
- What this involves →
IPO & acquisition planning
Most of the decisions worth making about an IPO or acquisition have deadlines that pass before the money arrives.
- What this involves →
Tax strategy
Most tax advice assumes you own a business. When your income is a paycheck, the levers are fewer, and using them depends entirely on timing.
- What this involves →
Executive compensation
Deferral elections, bonus timing, benefit choices, severance terms. Each one is a decision, and most of them default if you leave them alone.
This material is for general educational purposes only and is not intended as tax, legal, or investment advice. Neither GGM Wealth Advisors nor Cambridge provides tax or legal advice. Please consult a qualified professional about your specific situation. Estimates are illustrative, based solely on the figures you enter and simplified assumptions. Your actual results will differ.
Let's start with a conversation
Bring whatever is on your mind: a vest date you are unsure about, an offer you are weighing, a business you might sell in three years. Nothing to prepare, no cost, and you will leave with something useful whether or not we end up working together.
