Executive Retirement Planning
Deferred compensation schedules, restricted stock, option exercises, and concentrated positions, planned together with the rest of your retirement income.
The short answer
Executive retirement planning handles the parts of compensation that general retirement advice skips: deferred compensation distributing on a schedule elected years earlier, restricted stock, option exercises, and a concentrated position in the company that pays your salary.
An executive nearing retirement usually has the saving handled. What is left is compensation that does not behave like a 401(k).
Deferred compensation arrives on a timetable set years ago. A concentrated stock position carries a low basis and a trading window. Options have expiry dates. None of these appear in general retirement material, and for a senior executive they are often the largest items on the balance sheet.
What the work covers
Non-qualified deferred compensation
The distribution election was made at deferral, and Section 409A restricts changing it. Knowing that a large sum lands in a specific year changes what the plan does in the years before it. The balance also remains subject to employer creditor risk, which is a consideration in how much to defer going forward.
Restricted stock and purchase plans
Vesting creates ordinary income on a schedule. Holding after vest converts the position into a capital gains problem, and the basis is usually low.
Options
Incentive and non-qualified options are taxed differently and interact with the alternative minimum tax. Expiry dates remove the choice.
Concentrated position management
A multi-year unwind sized against bracket room, coordinated with charitable giving where it fits, and started before the retirement date rather than after it.
Who this is for
Senior executives at public or private companies, two to eight years from retirement, holding deferred compensation, equity, or both. Public-company executives carry the fullest version of it. Private-company equity adds valuation and liquidity questions, covered in what a buyout does to company equity.
Why it runs with everything else
Each of these competes for the same scarce resource: room under a tax threshold in a specific year. A deferred compensation payout consumes room a conversion was going to use. A stock sale raises income and can reduce a health insurance credit in the years before Medicare.
Solved separately, they tend to work against each other. That interaction is the subject of the four executive challenges essay.
Questions about executive retirement planning
Talk it through
Deferred compensation and equity decisions get harder the longer they wait, because the elections behind them are hard to unwind. The time to talk is while the schedule can still be planned around.
Nothing here is individualized tax or legal advice. Plan documents govern, and their terms differ.
Every engagement produces the same three things: a written retirement income plan, a multi-decade tax projection, and a coordinated Social Security and Roth conversion sequence. For both of you.
Schedule Your ConsultationEight pieces of one plan, not eight engagements. See how they fit together or the five phases that deliver them.
The other seven: Retirement Income Planning, Tax-Efficient Withdrawal Strategy, Roth Conversion Analysis, Social Security Optimization, Early Retirement Feasibility, Ongoing Retirement Tax Planning, Legacy Planning Coordination.
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