Scenario 1
A highly compensated employee vests RSUs throughout the year, but company withholding consistently falls short of the actual marginal tax rate. The advisor needs to prevent April surprises while still addressing concentration risk.
- Show how each vest affects taxable income, concentration, and projected shortfall.
- Compare immediate sale, staged sale, and hold scenarios against estimated tax payments and cash flow.
- Create a practical recommendation the client and CPA can use before the next vest hits.
Scenario 2
A client has double-trigger RSUs at a late-stage private company. The core question is not just value, but when the tax event occurs, when shares become liquid, and how fast concentration could build after the trigger is met.
- Map the timeline from trigger event to vesting, lockup, liquidity, and diversification decisions.
- Quantify the concentration and tax planning issues that appear once private RSUs convert into liquid stock.
- Give the advisor a client-ready action plan for the first 6 to 18 months after the event.