Case Study 01: The Corporate Executive

W-2 High Earner | Concentrated Equity | Deferred Compensation

THE SITUATION

A 56-year-old senior vice president at a regional healthcare company came to Flagship with a compensation package that most advisors had simply celebrated rather than examined. His base salary exceeded $400,000. He had accumulated significant unvested restricted stock units, a deferred compensation balance approaching seven figures, and a 401(k) that had grown substantially but was entirely in company stock. On paper, he was doing exceptionally well. In reality, he had no coordinated plan, and no one had ever looked at his entire financial picture at once.

THE CLARITY BUILDER — STARTING WITH WHY

The Clarity Builder conversation revealed something his prior advisor had never uncovered: he was two years from wanting to reduce his hours significantly, and he had a quiet but growing anxiety about what would happen to his lifestyle if the company's stock declined sharply. He had never said that out loud. Once he did, the entire planning conversation shifted. We were no longer optimizing a compensation package. We were building a plan for the life he actually wanted.

THE PANORAMIC PLANNING PROCESS

Mapped vesting schedules across RSUs, stock options, and deferred compensation to identify concentrated risk and tax-year exposure
Coordinated with his CPA to model the tax impact of exercising incentive stock options in a lower-income year versus a high-bonus year, and to evaluate AMT implications
Worked with a tax attorney to review his deferred compensation structure and distribution elections before an irrevocable deadline passed
Introduced a Donor Advised Fund to allow charitable giving with appreciated stock, reducing taxable income in high-earn years while preserving flexibility for future grants
Began a systematic diversification strategy using tax-loss harvesting to offset gains as RSUs vested
Implemented a direct indexing strategy within his taxable account: rather than holding a standard index ETF, he owns the individual underlying stocks directly through a separately managed account. This structure allows for systematic tax-loss harvesting at the individual stock level, generating realized losses that can offset capital gains from RSU vesting and option exercises. The goal is tax alpha: keeping more of the return after taxes rather than simply matching the index before taxes. Direct indexing is particularly powerful for high-income investors with ongoing capital gains events, where the tax drag of a traditional index fund or ETF would otherwise erode meaningful wealth over time.

TAX PLANNING VS. TAX ADVICE — HOW WE WORK

Tax planning at Flagship means we identify the strategy, model the timing, and coordinate the conversation. The actual tax return preparation and legal opinions were provided by his CPA and tax attorney. We ran point between all three professionals.

THE OUTCOME

Within 18 months, he had a clear vesting and exercise calendar, a deferred compensation distribution strategy aligned with his reduced-hours plan, and a diversified portfolio no longer dependent on a single employer's stock. He described it as the first time his financial life felt as intentional as his professional life.

This case study is a composite, anonymized vignette drawn from common planning patterns. No individual client or identifying information is represented. Results vary based on individual circumstances. This is not tax advice. Flagship Asset Services coordinates with CPAs, tax attorneys, estate attorneys, and other licensed professionals as part of a collaborative planning team. Tax planning is educational and strategic in nature; tax advice and tax return preparation are provided by qualified tax professionals.

Securities and Advisory Services offered through LPL Financial, a registered Investment advisor. Member FINRA/SIPC.