Equity Compensation Planning
Turn Opportunity into a Flightpath to Success
You’re a highflying executive trying to capitalize on the opportunities that success has brought you. You’re in a hurry to enjoy the fruits of your labor but time is a major barrier.
If asked when you’d like to retire, you’d say “Yesterday.”

WestStar’s advisors are highly experienced in helping equity-compensated professionals (we call them, “Aviators”) maximize their compensation programs and master the intricacies that come with being paid in complex ways.
Aviators at companies like Amazon, Apple, Boeing, Meta, Nike, Starbucks, and Oracle look to us to help them manage their stock programs and create investment and tax strategies to get them where they want to be.
Maybe you also want to get off the treadmill by age 55, or use the opportunity of an IPO to gain financial independence. Perhaps you have a growing family and are weighing up the trade-offs in giving them a great chance at life.
If you’re looking to make the most of your opportunities, let’s talk about how we can help you.
When we first chat with highflyers we find these 6 questions on their minds:
Am I doing everything I can to secure my family’s future?
Am I making the most of all the benefits offered to me?
What can I do to make sure my plan is crash-proof?
How long will it take to get set up for life?
How do I grow the resources I’ve built?
How soon can I find all of this out?
Use Your Equity to Really Fly!
Our free Equity Compensation Guide unpacks and explains how to help maximize your plans and benefits.

How we help optimize your Stock-based Compensation Programs
It’s difficult to take focused action without clarity.
One of the first questions we ask new clients is “what does your idea of a prosperous life look like?” We often find the answer to this is why they reached out to us. It also tells us what to pack into a financial plan that works as hard as you do to meet your goals.

We find most people are unaware of what they can create when their stock programs are managed with an understanding of their goals, timing of grants, and navigation of blackout dates.
One of the first questions we ask new clients is “what does your idea of a prosperous life look like?” We often find the answer to this is why they reached out to us. It also tells us what to pack into a financial plan that works as hard as you do to meet your goals.
Managing Vesting Schedules, Payouts, and Tax Strategies
Time stress is a common factor among tech pros and so we help you understand the key concepts along with terms and conditions of your grant. We also keep a close watch on timelines and vesting schedules.
Thankfully the timeline that governs the process is set out in vesting schedules that apply to almost all stock-based compensation packages.
– Time-based Vesting (includes Cliff Vesting)
– Mixed Vesting
– Graded Vesting
– Performance-based Vesting

The trick is to know the rules and restrictions, and precisely how your rewards can be of greatest benefit to you. Then, to turn the complex challenges into a clear flightpath to follow.
Our ‘advice in plain English’ approach also covers the tax implications surrounding your compensation programs and we help you make decisions with a long-term financial plan in mind.

Technology and Tools to Put You in The Pilot's Seat
Working with WestStar means you’ll have a co-pilot in your cabin. You’ll get to see your future through a professional’s eyes, and have the tools and tech you need on a digital platter.
Our Navigator 360° Flightpath is a strategic plan that defines your personal goals and outcomes, pinpoints priorities, and charts your routes to success. It also serves as a communication tool that articulates our strategic thinking in a clear, understandable, and actionable way.

A simulator beneath the dashboard measures your probability of success and we can create scenarios that chart your trajectory.
It’s an incredibly dynamic tool that makes a complex journey simple, easy to follow and perfectly clear. It brings your overall prosperity into focus: stock compensation, investments, savings, Social Security income, pension information, retirement plans and more.
Your Navigator 360° Flightpath is strategically reviewed throughout our journey together, tracking your progress and course-correcting when necessary.
Stock Concentration and Diversification
A concentrated stock risk occurs when you own a stock that represents a large percentage of your stock portfolio and your wealth becomes concentrated in this single stock.
How Much to Hold?
How Much to Sell?
How to Decide?
Read our handy article on managing concentrated stock risk.
According to your needs, we develop and implement a 360° Financial Plan that can also include the following planning essentials:



Relationships built on trust
At WestStar we believe that trust is earned. Our relationships are real, honest and candid. We say what we do, and we do what we say.
We tailor our interactions and communications according to your schedule and preferences.
Our personal touch and care is evident in all of our relationships, many of which have served our highflying clients and their families’ best interests for decades.
If that sounds like a relationship worth pursuing, then we would be delighted to partner with you in getting you to where you want to go on your flightpath.
The sigh of relief from our Aviator clients when we show them how their hard work and compensation programs can get them to their goals is always a special moment.
Our Equity Compensation Expertise Includes:
Non-Qualified Stock Options (NSO or NQSO) | Incentive Stock Options (ISO) | Restricted Stock | Restricted Stock Units (RSU) | Employee Stock Purchase Plans (ESPP) | Nonqualified Deferred Compensation (NQDC) Plans | Retention Bonuses | Performance Stock Units | Vesting Schedules | Managing Blackout Dates | Avoiding Concentrated Stock Risk | Tax Strategies and more!
Disclosures
All investing involves risk, including the possible loss of principal. There is no assurance that any investment strategy will be successful.
A diversified portfolio does not assure a profit or protect against loss in a declining market.
Equity Compensation Frequently Asked Questions
Equity compensation is also known as stock-based compensation. As such, it is a form of non-cash compensation and results in employees receiving ownership in the company, which serves to align employees’ interests with the firm’s success. Some examples of equity compensation include options, restricted stock units (RSUs), and employee stock ownership plans (ESOPs).
Equity compensation is non-cash pay that a company offers to its employees. Equity compensation comes in various forms and may include stock options, restricted stock, and performance shares; all of these investment vehicles represent ownership in the firm for a company’s employees. At times, equity compensation may accompany an otherwise below-market salary, since it offers employees the opportunity to benefit from their firm’s success.
Benefits for employees: The main advantage of equity-based compensation for employees is the potential financial reward and possibility of long-term wealth creation. Since the value of your equity is linked to your company’s stock price, your financial benefits could be more significant than fixed cash bonuses if your company succeeds and the stock price grows.
Employees are incentivized to contribute to the company’s success, since their own financial interests are tied to it. This alignment can lead to high-performing company cultures.
Benefits for companies: Companies offer equity in order to attract and retain talent: equity compensation can be a powerful tool for attracting and retaining the best of the best.
Reduced cash outflow happens when companies offer equity instead of cash, which can be beneficial during periods of financial constraints.
Equity compensation (such as stock options or restricted stock units (RSUs)) is calculated based on the number of shares granted to an employee, the exercise price (in the case of options), and the fair market value of the shares at the time of grant and vesting. Read on for a more detailed breakdown.
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Types of Equity Compensation:
Stock Options: Stock options give employees the right to purchase company shares at a predetermined price (the exercise price) for a set period of time.
Restricted Stock Units (RSUs): These are shares that are allocated to an employee and vest over time, meaning the employee gradually earns the right to own them.
Employee Stock Ownership Plans (ESOPs): ESOPs allow employees to own a portion of the company’s stock.
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Calculation Steps:
Grant: This is the start of the process: the company determines the number of shares or options to be granted to an employee.
Vesting: The equity typically vests over a period (e.g., 4 years), meaning the employee gradually earns the right to own or exercise the equity over time. There are different types of vesting schedules and these can be subject to a variety of time frames.
Exercise (for stock options): The employee must choose whether or not to exercise their options to purchase shares at the predetermined price.
Sale: Once vested (and exercised, if applicable), the employee can choose to sell their shares, subject to any restrictions the company has placed on the equity.
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Key Factors:
Fair Market Value: This is the value of the shares at the time of grant and vesting, and is crucial for determining the value of the equity compensation.
Exercise Price (for options): This is the price at which the employee can purchase the shares providing that they choose to exercise their options.
Vesting Schedule: The vesting schedule determines the time frame – how quickly the employee earns the right to own or exercise the equity.
Company Performance: The value of the equity compensation comes down to company performance and can fluctuate based on the company’s success in the markets.
Restricted Stock Units (RSUs)
Restricted stock units (RSUs) are by far the most common form of equity compensation. Both public and private companies offer it, and it is a favorite because it’s easier for employees to understand and easier for employers to administer than other types of equity at the company level.
Stock Options
Stock Options offer the right to purchase company stock at a predetermined price (the “strike price”) for a set period.
Employee Stock Ownership Plans (ESOPs)
An ESOP is a plan where employees purchase company stock, often at a discounted price, through payroll deductions.
RSUs are the most common type of equity award. In simple terms, they are a promise from the employer to grant company shares to their employees at a future date (or series of future dates) based on agreed criteria.
RSUs typically vest over a period of time. Some awards may be contingent on the company or the individual (or both) meeting specific performance marks.
Two taxes generally apply to employees’ equity earnings: ordinary income tax and capital gains tax. Typically, you’ll owe income tax on your equity in the tax years during which you acquire shares. Capital gains tax comes into play when you sell your shares.
Equity compensation is taxed differently based on the type of equity you receive. Here’s a breakdown of the most common types and tax considerations that apply:
- Stock Options: There are two main types of stock options – Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs/NQSOs).
Incentive Stock Options (ISOs): There is no tax at grant or exercise (unless subject to Alternative Minimum Tax (AMT)). ISOs are taxed at sale: The long-term capital gains (lower tax rate) applies if ISOs are held at least 1 year from exercise and 2 years from grant. Short-term capital gains (ordinary income rates) apply if ISOs are sold earlier.
Non-Qualified Stock Options (NSOs/NQSOs): There is no tax at grant. NSOs/NQSOs are taxed at exercise. The difference between the exercise price and fair market value (FMV) is taxed as ordinary income. Any further gain/loss at sale is taxed as capital gains.
- Restricted Stock Units (RSUs): There is no tax at grant. RSUs are taxed as ordinary income based on FMV at vesting. Any further gain (at sale) is taxed as capital gains (short- or long-term based on holding period).
- Employee Stock Purchase Plans (ESPPs): No tax at grant or purchase. Taxed at sale:
If held 2 years from grant & 1 year from purchase, part of the gain is taxed as ordinary income, and the rest as long-term capital gains. Otherwise, the entire gain is taxed as ordinary income.
- Restricted Stock Awards (RSAs): RSAs are taxed at vesting, unless an 83(b) election is made (to be taxed at grant instead). Taxed at sale: Any gain is capital gains.
Tax Withholding & Reporting
Employers typically withhold taxes on RSUs, NSOs, and RSAs at vesting/exercise. ISOs may trigger AMT liability at exercise.
Capital gains taxes apply upon sale.
Whether to sell your vested stock immediately or hold for long-term gains depends on a few key factors.
Reasons to Sell Immediately include:
Diversification: If a large portion of your portfolio is in your employer’s stock, selling can reduce risk.
High Stock Price: Locking in profits might be smart if the stock is at an all-time high or overvalued.
Need for Cash: If you need funds to cover expenses, selling could make sense.
Tax Implications: If the stock is classified as non-qualified stock options (NSOs), you may already owe taxes upon vesting. Selling prevents further risk.
To reduce risk / free up funds, many employees sell some vested stock immediately and hold the rest for potential growth.
For equity compensation to be a powerful wealth-building tool, it should fit strategically into your overall financial plan based upon your goals, risk tolerance, and tax situation.
Here’s how it can play a role in 5 areas of your financial plan:
- Wealth Building & Investment Strategy: Equity compensation can significantly increase your net worth. You should consider diversifying instead of keeping too much of your portfolio tied to your employer’s stock. And also, look to balance equity holdings with other asset classes like index funds, bonds, and real estate.
- Risk Management & Diversification: If a large portion of your wealth is in company stock, you face concentration risk – if the stock drops, so does your wealth. Selling vested shares over time and reinvesting in a diversified portfolio can reduce this risk.
- Tax Efficiency: Restricted Stock Units (RSUs) are taxed as ordinary income when they vest. Selling them immediately may not increase your tax burden. With stock options (ISOs & NSOs), tax treatment varies; ISOs get favorable capital gains treatment if held long enough. Employee Stock Purchase Plans (ESPPs) often offer a discount, but tax treatment depends on the holding period. Planning when to sell can help optimize taxes and maximize after-tax gains.
- Cash Flow & Liquidity: Equity compensation isn’t immediately liquid – until you sell, it’s just “paper wealth.” You should have a strategy to convert stock into cash if needed for short-term financial goals.
- Retirement Planning: Consider rolling gains from equity sales into tax-advantaged accounts (401(k), IRA) to secure long-term financial stability. Some executives also use net unrealized appreciation (NUA) strategies for employer stock in 401(k) plans.
A general rule of thumb is to limit your exposure to your employer’s stock to 10-15% of your total investment portfolio.
Here are the 3 key risks of holding too much employer stock
Concentration Risk – If your company underperforms or faces financial trouble, both your job and your investments could be at risk at the same time.
Lack of Diversification – A balanced portfolio should include different asset classes (stocks, bonds, real estate, etc.) to reduce risk of all your eggs in one basket.
Stock Volatility – Individual stocks, especially in tech or startups, can be highly volatile.
Here are 3 reasons to hold some employer stock
Belief in Company Growth – If you strongly believe in the company’s long-term potential, holding a portion may be beneficial.
Tax Benefits – Holding stock for over a year can qualify for long-term capital gains tax rates.
Dividends & Perks – Some employer stocks offer dividends or special employee incentives.
If your employer’s stock makes up more than 15-20% of your portfolio, consider gradually selling and reinvesting in a diversified portfolio to manage risk.
Disclosure
A diversified portfolio does not assure a profit or protect against loss in a declining market.