Wealth Management for Executives & C-Suite
Your compensation package is complex. Your financial plan should be too. We work with senior leaders at Fortune 500 and large public companies — at the intersection of executive compensation, tax strategy, and long-term wealth.
Client Profile
Meet Jennifer
Jennifer is a CFO at a publicly traded biotech company. She earns a $500K base salary, receives $1.2M in RSUs annually, participates in a non-qualified deferred compensation plan, and holds significant ISO options. She has a concentrated position in company stock and a complex tax situation that changes every year as equity vests. She's worked with three advisors over twelve years and never felt like any of them truly understood the nuances of her compensation — until she found a specialist.
These are hypothetical scenarios for illustrative purposes only and do not represent actual clients or results.
The Challenges You Face
Equity Tax Complexity
RSUs taxed as ordinary income, ISOs with AMT exposure, NSOs at exercise — each works differently, and the wrong decision at the wrong time can be costly.
Concentrated Stock Risk
Years of RSU vesting have created a portfolio dominated by company stock. Diversifying requires a careful strategy: trading windows, 10b5-1 plans, and tax-aware liquidation schedules.
Deferred Compensation Complexity
Distribution elections must be made years in advance and are generally irrevocable. The wrong choices lock in a suboptimal tax outcome for decades.
Time and Bandwidth
Running a company or leading a division leaves little time for the financial expertise your compensation package demands. You need a partner who handles the complexity so you don't have to.
Blackout Windows
Trading blackout periods restrict when you can sell company equity. Your financial plan must work within these constraints while still achieving your diversification goals.
Holistic Coordination
Your CPA files your taxes. Your estate attorney wrote your trust. Nobody has looked at all of it together. The gaps between advisors are where wealth is lost.
How Diamond Mountain Financial Helps
Comprehensive Equity Audit
We build a complete picture of your equity compensation: RSU vesting schedule, option strike prices and expiration dates, ESPP enrollment, deferred comp elections, and the tax impact of each. Most executives have never seen all of this modeled together.
Tax-Optimized Vesting and Exercise Strategy
We model the tax impact of different RSU sale timing, ISO exercise scenarios (including AMT planning), and deferred comp distribution elections. We identify the strategies that minimize your total tax burden across multiple years, not just the current filing.
10b5-1 Plan Coordination
For executives with insider trading restrictions, a well-structured 10b5-1 trading plan allows you to diversify on a pre-arranged schedule regardless of blackout windows. We coordinate the plan with your legal counsel and ensure it aligns with your tax and investment strategy.
Concentrated Position Diversification Roadmap
A multi-year plan to reduce your company stock concentration in a way that balances tax cost, diversification pace, and trading constraints. We model multiple scenarios and recommend the right cadence for your situation.
Integrated Wealth Plan
All of the above is coordinated with your estate plan, insurance coverage, retirement savings, and personal goals. Every dimension of your financial life works together — not in silos.
Frequently Asked Questions
How do I manage RSUs and avoid a large tax bill?
RSUs are taxed as ordinary income at vesting — there's no avoiding that initial tax. The strategy is what comes next: sell timing to offset with losses elsewhere, charitable contribution of appreciated shares to a donor-advised fund, and coordination of multiple vesting events across years. A structured multi-year plan consistently outperforms ad-hoc decisions.
What is a 10b5-1 trading plan and when should I use one?
A 10b5-1 plan is a pre-arranged schedule for selling company stock that provides an affirmative defense against insider trading claims. It allows executives to sell shares on a regular schedule during blackout windows — as long as the plan was established when you didn't possess material non-public information. It's particularly valuable for executives with large concentrated positions and frequent trading restrictions.
How does Diamond Mountain Financial help executives optimize deferred compensation?
Deferred comp decisions are often irreversible — distribution timing elections must typically be made a year or more in advance and cannot be changed. We model your projected tax rates in retirement, evaluate your employer's credit risk, and help you make distribution timing elections that fit your retirement income plan. Getting this right can meaningfully reduce lifetime tax cost.