EQUITY, TIMING, AND TRADE-OFFS

Services for C-Suite Professionals

You've built something great. Let's make sure it's working for you.

By the time you reach the C-suite, the hard part isn’t earning — it’s everything attached to the earning. Equity grants with vesting schedules and exercise windows. Deferred compensation you elected into years ago. A concentrated position in your own company’s stock. Benefits and perquisites that look generous on paper and are easy to leave on the table.

These pieces interact. A decision about when to exercise options changes your tax picture, which changes what you should do with your deferred comp election, which changes how much risk you’re carrying in a single stock. Handled separately, they work against each other. Handled together, they compound.

We help executives see the whole picture and make decisions in the right order — with an eye on the fact that this phase of your career, however long it lasts, is the one that funds everything after it.

Options, RSUs, performance shares, and ESPPs each behave differently, and the differences matter most at the moments you’re least likely to be paying attention — a vesting date, a blackout window closing, an expiration you assumed was further out.

We map what you hold, when it vests, what triggers a tax event, and what happens to each grant if you leave, retire, or the company is acquired. From there the real question is strategy: when to exercise, when to sell, and how to build a disciplined schedule rather than reacting to the stock price. Executives are often subject to trading windows and pre-clearance, so timing has to be planned well ahead of when you’d like to act.

Success often means a large share of your net worth tied to the same company that pays your salary and funds your retirement plan. If the company struggles, all three move together.

Reducing that concentration is rarely as simple as selling. There are tax consequences, ownership guidelines you may be required to meet, optics with your board and colleagues, and the genuine belief you likely hold in the company’s future. We help you set a target — how much exposure is reasonable given everything else in your plan — and then get there deliberately, through scheduled selling, charitable strategies, or diversification of new money. The goal isn’t to bet against your company. It’s to make sure one outcome doesn’t determine all of them.

Non-qualified deferred comp is one of the most powerful tools available to you and one of the easiest to mishandle. Election windows come once a year, distributions lock in long before you need the money, and the balance is generally an unsecured claim against your employer.

We help you decide how much to defer and how to structure distributions so income arrives when your rate is likely lowest. The same review covers supplemental retirement plans, executive disability and life coverage above group limits, and the benefits most executives elect once and never revisit. We go through your full package annually — plan features change, and open enrollment moves faster than it should.

Executive compensation creates tax events on a schedule you don’t control, which makes planning ahead the only real lever. Filing looks backward. Planning looks at the next several years at once and decides what to accelerate, defer, or spread out.

That means coordinating exercise and vesting across tax years, managing the AMT exposure that incentive stock options can create, and using charitable giving strategically in high-income years. We work alongside your CPA rather than replacing them — so nothing gets discovered in March that could have been solved in September.

Executive departures are rarely clean. Severance, a final equity payout, deferred comp distributions, and a consulting arrangement can all land in the same twelve months — and how you sequence them is worth real money.

We plan for that window before you’re in it: what accelerates on departure, what you forfeit, how a non-compete affects what comes next, and where your income will come from once the paycheck stops. Then we build the retirement income side with flexibility in it — pre-tax, Roth, and taxable assets, so you can manage your bracket year to year instead of taking what you’re handed.

Zero Expectations

Zero Pressure

Zero Judgement

Zero Commitment

Zero Cost

Zero Strings