The Client Challenge

A Senior Vice President at a pre-IPO enterprise software firm was facing a massive liquidity event. With $4.5M in dual-trigger RSUs vesting upon the company's public debut alongside exercise-and-hold ISOs, the client was looking at an estimated federal and state tax bill exceeding 50% on peak income. Their prior tax preparer only offered year-end compliance reporting, leaving the executive entirely unprotected against a massive tax hit.

The Citadel Strategy

Citadel Partners custom tailored a Strategic Tax Blueprint to build a multi-year execution framework starting 12 months prior to the IPO date:

• Section 83(b) & ISO Staging: Structured a phased exercise schedule for remaining Incentive Stock Options to maximize the $100K annual limit and optimize Alternative Minimum Tax (AMT) crossover points.
• Charitable Lead Annuity Trust (CLAT): Integrated a funding strategy utilizing highly appreciated stock post-IPO, creating a immediate high-bracket deduction while retaining residual wealth for the family's beneficiaries.
• Qualified Small Business Stock (QSBS) Audit: Verified historical holding periods across early-stage equity grants to secure maximum exclusion under IRC §1202.

The Measurable Impact

• $1.12M in Total Tax Savings realized across a 3-year execution window.
• Zero AMT Surprise: AMT liability was completely mapped and offset using timely charitable deductions and harvest strategies.
• Ongoing Partnership: Upgraded to the Private Client Group for long-term equity monitoring and wealth preservation.