Equity Compensation Planning

Equity compensation planning is deciding when to vest, exercise, sell, and diversify, with the tax consequences modeled before you act instead of discovered afterward. It covers RSUs, ISOs, NSOs, RSAs, ESPPs, and concentrated positions.

You worked hard for your equity. Most people never have a real plan for it.

RSUs sold at the default withholding rate. ISOs unexercised because nobody explained the AMT risk. A liquidity event that arrived without a plan. These are not rare mistakes. They happen to capable, successful people.

At Concierge Wealth Management, equity compensation planning is not an add-on. It is a core part of how we manage your financial life.

What Equity Compensation Do We Help You Plan For?

Restricted Stock Units (RSUs)

Taxed as ordinary income at vesting, often withheld at a flat rate that does not reflect your actual bracket. We work with you before vesting so nothing surprises you at tax time.

Incentive Stock Options (ISOs)

Favorable tax treatment, but only if navigated correctly. Exercise timing, AMT exposure, and qualifying dispositions interact in ways that create either significant savings or significant surprises. We model the scenarios before you act.

Non-Qualified Stock Options (NSOs)

Taxed as ordinary income at exercise. The spread hits your W-2 immediately and can push you into higher brackets or trigger other income thresholds. We help you time exercises strategically.

Restricted Stock Awards (RSAs) and the 83(b) Election

An 83(b) election made within 30 days of grant can be one of the most valuable tax decisions an early employee or founder makes. Miss the window and it is gone permanently.

Employee Stock Purchase Plans (ESPPs)

The discount is an immediate return. But holding periods, disposition rules, and concentration risk matter. Under-contributing and holding too long are both common. We help you avoid each.

Concentrated Stock Positions

A single position representing a significant portion of your net worth is both an opportunity and a risk. We build disciplined, tax-efficient diversification strategies that protect what you have built.

10b5-1 Plans

If you are an officer, director, or subject to trading windows, a 10b5-1 plan lets you sell on a pre-set schedule established while you are not aware of material non-public information. The rules changed in 2022 and now include mandatory cooling-off periods before trading can begin. Set up correctly, diversification happens systematically rather than whenever a window opens.

Liquidity Events

IPOs, acquisitions, and tender offers all require decisions made under time pressure. Pre-event planning is everything. If a liquidity event is on your horizon, now is the time.

What Does Waiting Cost? One Client Lost $1.1 Million

Kevin held $2,800,000 in a single company stock. Nearly 70% of his investable assets. He was hesitant to sell, worried about the tax bill, confident the stock would keep climbing.

We recommended a systematic diversification strategy. He chose to hold.

The position fell 40% over the next 18 months. More than $1,100,000 gone, and retirement pushed back years. The tax bill he was avoiding would have cost a fraction of that.

We cannot predict markets. We can build a plan that does not depend on being right about them.

How Does Equity Compensation Planning Work?

Every equity decision is evaluated in the context of your complete financial life. Income, portfolio, cash flow, family priorities, long-term goals. Coordinated with your CPA, integrated into your investment strategy, built around your actual life.

One point of coordination. Nothing falls through the cracks.

Who Needs Equity Compensation Planning?

A high earner in your 30s, 40s, or 50s with a meaningful equity grant. A senior executive managing multi-year vesting schedules. A professional navigating a liquidity event. Someone who already has an advisor but suspects the equity comp piece is not being handled well.

If equity compensation plays a meaningful role in your financial life, you need someone who understands it deeply and manages it deliberately.

We do.

Where Do Your Clients Work?

Our clients hold equity at Google, Amazon, Microsoft, Oracle, Meta, Uber, Mastercard, Shopify, Anthropic, Vertex, CrowdStrike, and DraftKings, along with several other Boston-area biotech and life sciences companies. Pre-IPO and public.

What Happens If You Wait?

Equity decisions expire. An 83(b) window closes in 30 days. ISO exercise timing shifts your AMT exposure year by year. A vesting tranche you did not plan for is taxed at whatever your employer withheld.

None of those are reversible after the fact. All of them are manageable before.

Your equity should work as hard as you did to earn it. 📈