Executives with Equity Compensation
Your net worth is in one place.
For senior executives, founders, and early employees whose wealth is in one company — Public or private, the rules change — The plan has to speak that language.
§ 01 / Opening
The upside is real. So is the concentration.
Equity compensation is one of the most powerful wealth-building tools in the American economy. It's also one of the most mismanaged. The IRS rules are dense, the vesting schedules compete with blackout windows, and the decisions are irreversible — an exercise made in the wrong quarter, an 83(b) missed at grant, a concentration held too long through a drawdown. Each one creates consequences that can't be undone by the time they show up on a tax return.
For most executives with significant equity, the stock isn't an investment. It's a life. The compensation funds the household, the taxes, the lifestyle, the future. It's also tied to a single company whose performance you don't fully control, whose direction you can only partially influence, and whose blackout calendar dictates the days you can actually act.
Equity compensation is often treated as a line item in a broader plan. At Rockline, it's treated as a discipline the firm was built around — because for the clients who come to us with RSUs, ISOs, and concentrated stock, the equity is the plan until we've built something better.
§ 02 / The Work
Six capabilities. Technically integrated.
Equity compensation strategy.
RSUs, ISOs, NSOs, PSUs, ESPP, deferred compensation, restricted stock, phantom stock — each with its own tax mechanics, vesting rhythm, and decision points. We model the scenarios so that exercise, sale, and hold decisions happen with full visibility into the multi-year tax consequences. Before the quarter closes. Not after.
Concentrated stock management.
For executives whose net worth is heavily weighted in a single position, diversification is a multi-year discipline, not an event. Systematic sell programs, hedging strategies, exchange funds, charitable offset strategies. We build the diversification plan around your blackout calendar, your tax capacity, and your view on the company's trajectory.
10b5-1 plan coordination.
Structured trading plans that let you sell systematically during blackout windows while staying compliant with your company's insider trading policy and SEC requirements. We work with your legal counsel to structure plans that align with your diversification goals and disclosure obligations.
Multi-year tax positioning.
AMT modeling for ISO exercises. Bracket management across multi-year exercise plans. Charitable timing strategy for appreciated stock. QSBS analysis for early-stage equity. All coordinated with your CPA before the decisions get locked in.
Integrated wealth planning.
Your equity comp strategy doesn't exist in a vacuum. It connects to your investment portfolio, your estate plan, your cash flow, your insurance, and your family's long-term goals. Every move we make is coordinated across the whole plan.
Ongoing coordination.
New grants, promotions, company events, regulatory changes, life events — the strategy evolves with them. We stay in sync with your equity administrator, your legal counsel, and your CPA so the architecture holds up as your career unfolds.
§ 03
The decisions are irreversible. The planning has to happen before they're made.