Stock Options & Employee Benefits

Stock Options & Executive Benefits

Maximize your equity. Minimize your tax. Protect your upside.

If your income goes beyond base salary – stock options, RSUs, deferred comp, ESPPs or mega-backdoor Roths – you know the upside is huge. But so are the risks, tax consequences and missed opportunities if you’re not planning around them.

We help high-performing professionals and executives optimize their total comp package, avoid painful tax surprises, and build long-term wealth from their equity.

Who We Serve

We work with pre-retirees, tech employees, corporate execs, and entrepreneurs to help the make smart, tax-optimized decisions around their complex compensation.

You earned it. Let’s make sure you keep more of it.

What You Gain

A clear, tax-efficient strategy for exercising and selling stock

Reduced exposure to market swings or single-stock risk

Confidence that your benefit package is fully working for you

Integration of equity and comp decisions with retirement, tax and estate plans

A smart, experienced partner to model trade-offs and answer “what-if” questions

Equity Compensation Planning

We analyze and time your equity decisions to help you extract the most value.

We Help You:

Strategically exercise ISOs and NSOs to minimize AMT and regular tax

Optimize RSU liquidation and tax withholding schedules

Model alternative minimum tax (AMT) exposure in years of large ISO exercises

Decide between early exercise vs. post-vesting (83)(b) election)

Coordinate with your CPA to avoid triggering surtaxes (NIIT, Medicare, etc.)

Tax-Efficient Liquidation Strategies

Your shares are valuable – but also taxable.

We Help You:

Create a diversification plan that reduces concentration

Time sales with capital gains treatment in mind (1+ year holding periods)

Harvest Tax Losses to offset large gains when possible

Build tax-efficient portfolios with proceeds from equity sales.

Layer in charitable giving (e.g. gifting appreciated shares to donor-advised funds)

Executive Benefit Plan Reviews

You’ve got great benefits – now let’s make sure you’re getting the most out of them.

We analyze and advise on:

Deferred compensation plans: cash flow modeling, payout schedules, risk analysis

Supplemental Executive Retirement Plans (SERPs)

Mega Backdoor Roth strategies inside 401(k) plans

Health Savings Accounts (HSAs) as stealth IRAs

Executive disability and life insurance integration

Decision Support Before Major Career Moves

Whether you’re changing companies, receiving a promotion, or prepping for IPO/liquidity, we will help you plan accordingly.

We Provide:

Pre-IPO planning (QSBS, AMT, blackout periods, lockups)

Exit package analysis (severance, COBRA, unvested equity)

Offer letter reviews for new roles with complex equity

Tax bridge planning if you’re taking time off between jobs

Common Mistakes We Help You Avoid

Forgetting to adjust 401(k)/HSA contributions as income fluctuates

Waiting too long to exercise ISOs and getting hit with AMT

Selling RSUs without a tax strategy and losing 40% to the IRS

Concentrating too much in company stock and ignoring downside risk

Missing the 83(b) election window and paying unnecessary taxes later

Why Work With Us:

We get it – your compensation isn’t just about today’s paycheck. You’re building something bigger. We speak the language of stock options, IPOs, vesting schedules and benefit cliffs. We also partner with your CPA, estate attorney and HR benefits team to make sure your plan is coordinated, not siloed.

We build the strategy yours deserves.

Equity Plans don’t come with a manual.

Real Tax-Efficient Outcomes

A retiring Coca-Cola exec came to us with 5+ stock plans, no tax strategy, and a looming liquidity event. We optimized timing, modeled AMT impact, and saved over $300K in taxes while reducing concentration risk by 60%.

Ready to Turn Complex Compensation into Lasting Wealth?

Great compensation can become a great liability – without a plan.

Schedule A FREE Consultation