Stock Compensation Planning

Restricted Stock Units (RSUs). RSUs are taxed as ordinary income at vest, which means every vesting event is a tax event. The timing of sales, the coordination with other income sources, and the decision of whether to hold or sell immediately all have significant tax and wealth implications. We build a vesting-aware plan that coordinates RSU income with your broader tax strategy.

Incentive Stock Options (ISOs). ISOs offer the potential for favorable long-term capital gains treatment, but they also create AMT exposure that catches many employees off guard. The exercise decision — when, how many, and in what tax year — requires careful modeling. We run multi-year tax projections to help you exercise strategically and avoid unnecessary AMT liability.

Performance Stock Units (PSUs). PSU payouts depend on company performance metrics and can vary dramatically from target. The uncertainty makes planning harder — but not impossible. We model multiple payout scenarios and help you plan for the tax impact regardless of where the final number lands.

Employee Stock Purchase Plans (ESPP). ESPPs typically offer a 15% discount on company stock, making them one of the most reliable wealth-building benefits available. But the tax treatment depends on holding period, and the concentration risk compounds over time. We help you maximize the benefit while managing the risk.

Non-Qualified Deferred Compensation (NQDC / 457). NQDC plans require irrevocable elections made well in advance, and the consequences of getting the election wrong can be severe. Deferral amounts, distribution timing, and investment elections all need to be coordinated with your total financial picture. We help you make these decisions with full visibility into how they affect your cash flow, taxes, and long-term wealth.

Tax coordination. We don't plan each compensation type in isolation. RSUs, ISOs, ESPP, NQDC, and your regular W-2 income all flow into the same tax return. We build a unified tax strategy that coordinates across all compensation types to minimize your total tax burden over time — not just in a single year.

Concentration risk management. When a significant portion of your net worth is tied to a single stock, your financial future is correlated with your employer's performance. We build a diversification timeline that reduces concentration risk systematically — balancing tax efficiency with prudent risk management.

Exercise and sale timing. The decision of when to exercise options or sell vested shares isn't just about the stock price. It's about your total income in the year, your AMT position, your capital gains situation, and your long-term goals. We model multiple scenarios so you can make these decisions with confidence rather than guessing.

Cash flow planning around vesting. Equity compensation creates lumpy income. Large vesting events can spike your tax bracket, while gaps between vests can create cash flow challenges. We smooth this out with proactive cash flow planning that accounts for the timing and tax impact of every vesting event.

Integration with your full financial plan. Stock compensation planning doesn't exist in a vacuum. It connects to your retirement savings strategy, your investment allocation, your estate plan, your tax plan, and your goals for financial independence. We make sure every equity decision is made in the context of your complete financial picture.