A Comprehensive Guide to Stock Options in the US for Employees‍

Casey Fenton


September 12, 2023

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Suppose you're a top software engineer based in Bangalore, India. You've just received an attractive job offer from a promising start-up in Silicon Valley. While the salary is competitive, there's something else in the compensation package that catches your eye—stock options. Suddenly, images of Silicon Valley millionaires dance in your head. But what does this mean, and how does it work in your context as a non-US resident?

The concept of stock options as part of an employee compensation package is a tried-and-tested strategy that many US-based companies have employed. It has helped organizations from burgeoning startups to behemoths like Google retain their talent and encourage a culture of ownership and commitment. The potential of owning a piece of the company you work for can be highly motivating, leading you to contribute your best efforts towards the success of the business.

However, understanding the complex labyrinth of stock options, especially from a cross-border perspective, can be daunting. This comprehensive guide is crafted to help employees grasp the intricacies of stock options offered by a US-based employer, their underlying price structure, the implications of the fair market value, and more. 

Read on so you can gain insights into how stock options work, their legal and tax implications, and how they are unique in the US context compared to other countries. With an updated understanding of these complexities, you can leverage your stock options to potentially build a path to future pay and secure financial stability.

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Understanding Stock Options

In essence, a stock option, as part of an employee stock purchase plan, is a contract or employment agreement that grants you—the employee—the right, but not the obligation, to purchase company stock at a pre-determined price (the strike price) within a specified timeframe. This strike price is often set at the fair market value of the company's stock on the day the options are granted.

When a company grants you stock options, it's essentially giving you the right to 'bet' on the future increase of the company's stock price without risking your own money upfront. Theoretically, if the company performs well, the stock's market value will rise, and the value of your stock options will increase proportionately.

There are two potential scenarios:

  • If the stock price rises above the strike price (the price at which you can buy the stock), you can exercise your right to buy the shares at the discounted price and then, if you wish, sell them at the current market price for a profit. This is the essence of the employee stock option plan—allowing employees to purchase company stock at a price below its current market price, potentially leading to significant financial gain.

  • If the stock price does not exceed the strike price before the expiration date, your options will become worthless and expire. In this scenario, while you don't gain, you also don't lose anything other than the potential upside you would have realized if the stock price had increased.

A unique aspect of stock options is the vesting schedule, which will be discussed in the next sections. For now, it's essential to understand that vesting means you earn the right to exercise your options over time, rather than all at once.

Stock options can seem like a golden ticket to financial prosperity, particularly when a company's stock price is on the rise. However, they also come with complexities and risks. These include tax implications and the potential for options to become worthless if the company's stock price does not perform as expected.

Types of Stock Options

In the United States, there are two primary types of employee stock options: Incentive Stock Options (ISOs) and Non-Statutory Stock Options (NSOs), also known as Non-Qualified Stock Options (NQSOs). Both types offer the opportunity for employees to purchase company stock, but they have different rules and tax implications.

1. Incentive Stock Options (ISOs)

ISOs, often included in an employee stock purchase plan, are a form of equity compensation that provides special tax treatment under the Internal Revenue Code. Only employees of the company can receive ISOs.

A critical aspect of ISOs is that they can potentially provide more favorable tax treatment if certain conditions are met. Namely, if an employee holds the stock for at least one year after the exercise date and two years after the grant date, any gain realized on the sale of the stock will be treated as a long-term capital gain, which is typically taxed at a lower rate than ordinary income.

2. Non-Statutory Stock Options (NSOs)

NSOs, on the other hand, can be granted to employees, directors, contractors, and consultants. They do not provide the same tax benefits as ISOs.

When you exercise NSOs, the difference between the market price and the strike price (often referred to as the bargain element) is treated as ordinary income and is subject to withholding taxes. When you sell the stock, any additional gain above the fair market value at the exercise date is taxed as a capital gain.

It should be noted that while ISOs can provide more favorable tax treatment, they are also subject to the Alternative Minimum Tax (AMT), which can significantly complicate your tax situation.

Benefits of Incentive Stock Options (ISOs)

ISOs can provide several key benefits that make them an attractive component of an employee's compensation package. 

  • Potential for Long-Term Capital Gains: The most significant benefit of ISOs comes from their potential tax treatment. If you hold the stock for at least one year after exercising the options and two years from the grant date, the gain on sale is taxed at long-term capital gains rates, which are generally lower than ordinary income tax rates. This aspect makes ISOs potentially more tax-efficient than NSOs.

  • No Upfront Tax Liability: When you're granted ISOs, there's no immediate tax liability. Taxes come into play when you exercise the options and later when you sell the stock. This deferral of tax allows you more control over when and how you pay taxes on your options.

  • Potential for Higher Profits: If the company's stock price increases significantly, ISOs can lead to substantial financial gain. You get the right to purchase the stock at the strike price, which is locked in at the grant date. If the stock's market value rises above the strike price, the difference is your gain.

However, ISOs are not without their complexities and potential disadvantages. While they can provide considerable financial benefit, it's essential to understand the potential drawbacks associated with them.

Now, what could be the possible downsides of Incentive Stock Options (ISOs)?

  • Alternative Minimum Tax (AMT): The main downside of ISOs is the potential for Alternative Minimum Tax. The spread (difference between the fair market value on the exercise date and the strike price) on ISOs can be subject to the AMT, which can lead to a significant tax bill in the year you exercise the options, even if you don't sell the stock.

  • Risk of Decrease in Stock Price: Like any equity-based compensation, ISOs carry the risk of market volatility. If the company's stock price falls below the strike price, your options could end up "underwater," meaning they have no intrinsic value.

  • Liquidity Concerns: If the company is not publicly traded, it may be challenging to sell the stock you acquire through exercising ISOs. In such cases, you might need to wait until a liquidity event, such as a public offering or acquisition, to sell your shares.

  • Complexity of Tax Rules: The rules and tax implications surrounding ISOs can be complex. This complexity can make it challenging to make optimal decisions about when to exercise and sell the options. It's essential to consult with a tax advisor or financial advisor to help navigate these complexities.

Benefits of Non-Statutory Stock Options (NSOs)

NSOs, though they do not come with the same potential tax benefits as ISOs, can still offer significant advantages as part of your compensation package:

  • Flexibility of Recipients: Unlike ISOs, NSOs can be granted to anyone associated with the company, including employees, consultants, advisors, and board members. This flexibility makes NSOs a useful tool for companies to attract and retain a variety of talent.

  • No Alternative Minimum Tax (AMT): Unlike ISOs, the spread on NSOs at exercise is not subject to the Alternative Minimum Tax. This aspect simplifies tax planning, as you don't need to worry about a potential AMT liability.

  • Potential for Financial Gain: Like ISOs, NSOs offer the potential for financial gain if the company's stock price increases. You have the right to purchase the stock at the strike price, allowing you to benefit from any increase in the stock's market value above this price.

Despite these advantages, NSOs also come with their own set of potential downsides.

  • Ordinary Income Tax at Exercise: The main drawback of NSOs is that the spread at exercise is taxed as ordinary income. This tax treatment contrasts with ISOs, where the spread at exercise can be taxed as a capital gain if certain conditions are met.

  • Employment Termination: In many cases, if your employment contract ends, you may have a limited period (commonly 90 days) to exercise your NSOs. This constraint can create a financial burden if you have a significant number of options and a high exercise price.

  • Market Volatility Risk: Similar to ISOs, NSOs are not immune to the risk of the stock's market value decreasing. If the market price falls below the strike price, your options could end up "underwater," rendering them worthless.

  • Potential Liquidity Issues: If your employer is a private company, you may face difficulties selling your shares after exercising your NSOs, unless the company goes public or is acquired.

As with ISOs, the complexities surrounding NSOs necessitate expert advice. Make sure you consult with a tax advisor or financial advisor who understands these types of compensation plans. They can help you navigate the risks and take full advantage of the potential benefits of your NSOs.

Employee Stock Purchase Plan (ESPP): A Stock Options Derivative

While the focus is on stock options (both ISOs and NSOs), it's also important to mention another prevalent form of equity compensation in the US— the Employee Stock Purchase Plan or ESPP. Like stock options, ESPPs offer a way for employees to become shareholders in the company and potentially share in its success. However, they work differently than stock options and can offer their own unique benefits.

An ESPP is a program that allows employees to purchase company stock, often at a discounted price. Unlike stock options, where the employee has the right to buy the stock at a specified price in the future, an ESPP typically involves the actual purchase of stock at regular intervals.

Here's how ESPPs usually work:

  • Enrollment Period: At the start of the ESPP offering period, employees choose to participate by enrolling in the plan and determining how much of their paycheck they'd like to contribute, up to the maximum limit set by the employer and federal regulations.

  • Accumulation Period: Throughout the offering period (often six months), the payroll deductions accumulate in an account for each participant.

  • Purchase Date: On the purchase date, the employer uses the accumulated funds to purchase company stock for the participant. The purchase price is often discounted, typically by 10-15% from the market price, which can provide a significant benefit to employees.

One of the significant benefits of ESPPs is that they are typically easier to understand than stock options and provide a straightforward way for employees to own a piece of their company.

Moreover, ESPPs offer potential tax advantages. While the discount received on the purchase is technically taxable income, it's usually not taxed until the employee sells the shares. If the shares are held for more than one year after the purchase date and two years after the beginning of the offering period, any further gain is taxed as a long-term capital gain, which can be advantageous compared to ordinary income tax rates.

What is Stock Vesting

One of the essential aspects to understand about stock options, including both ISOs and NSOs, and even restricted stock units (RSUs) and ESPPs, is the concept of vesting. This process determines when you can exercise your stock options or when your stock or RSUs are truly yours.

Typically, when your employer grants you stock options, you don't get the right to use them immediately. Instead, you earn this right over a certain period — this is what "vesting” means.

Vesting generally works this way:

  1. Vesting Schedule: The most common type of vesting schedule is "graded vesting." In this setup, a certain percentage of your stock options vest each year over a set period. For example, your contract or employment agreement might state that 25% of your options will vest each year over four years.

  1. Cliff Vesting: Some companies use what's known as cliff vesting. In this scenario, you need to stay with the company for a certain period before any options vest. For instance, your options may not vest until you've been with the company for one year. After this "cliff," the remaining options may vest monthly, quarterly, or annually.

  1. Accelerated Vesting: In some cases, vesting might accelerate, meaning a larger portion of your options will vest sooner than initially scheduled. This acceleration often occurs in scenarios such as a company acquisition or the meeting of certain company performance milestones.

Once your options vest, you can choose to exercise them, which means you use your own money to purchase the shares at the stated price (strike price or grant price). The stock you acquire is yours to keep, even if you leave the company.

However, there's an essential aspect to consider here. If you leave the company before your options vest, typically you lose them. That's why it’s imperative to know your vesting schedule and consider it in your career and financial planning.

It's worth noting that ESPPs and RSUs also have vesting rules, but they can operate differently than stock options. For ESPPs, vesting often refers to the period you must hold the stock to receive favorable tax treatment. RSUs vest in a similar way to stock options, but once RSUs vest, they convert into actual shares of stock, unlike stock options where you must choose to exercise.

The bottom line: Vesting is a paramount aspect of your equity compensation. Always refer back to your employment agreement or consult a financial advisor to understand the specifics of your vesting schedule. This understanding will help ensure you're making the most of your employee stock options, RSUs, or ESPPs.

Legal and Tax Considerations for Stock Options

Navigating the complexities of stock options can be challenging, particularly when it comes to the legal and tax implications. Whether you're dealing with ISOs, NSOs, or even ESPPs, there are several key considerations that you should be aware of:

Ordinary Income vs. Capital Gains

One of the major differences between ISOs and NSOs lies in how they are taxed. When you exercise an NSO, the difference between the fair market value of the stock and the exercise price (known as the "bargain element") is taxed as ordinary income. For ISOs, this bargain element isn't taxable as ordinary income if you meet certain holding requirements. However, it is subject to the Alternative Minimum Tax (AMT).

Capital Gains Tax

If you hold the stock acquired through the exercise of any stock option for more than one year, any gain over the fair market value on the exercise date is usually considered a long-term capital gain when you sell the shares. This tax rate is generally lower than the rate for ordinary income.

Alternative Minimum Tax (AMT)

As mentioned above, ISOs are subject to the AMT, which can potentially negate some of the tax benefits. This can be a complex area, and you should consult a tax advisor to understand the potential implications.

Employment Agreement

Your employment agreement or the contract detailing the stock option grant will provide necessary details about your options, including the exercise price, number of options granted, vesting schedule, and what happens if you leave the company or if the company is sold. Make sure to review these documents thoroughly.

Exercise Price and Selling

When and how you exercise your options and sell the stock can have significant tax implications. A common strategy is to exercise and hold ISOs until you can qualify for long-term capital gains tax, but this strategy comes with its own risks, such as the potential for the stock price to fall.

Stock Options in Retirement Plans

While stock options cannot be transferred into a traditional retirement account like an IRA or 401(k), some employers offer a stock-based retirement program, where stock option gains can be deferred. This plan can have significant tax advantages, but it's relatively rare and has its own complex rules.

Fair Market Value

Fair Market Value (FMV) is an important metric for your stock options. It represents the price at which your company's stock is being traded on the open market. This price plays a pivotal role in determining the 'bargain element', which is the difference between the FMV and the exercise price when you exercise the options. If you're handling NSOs, this difference is considered taxable income, regardless of whether you sell the shares. As for ISOs, this difference is critical for calculating the potential Alternative Minimum Tax. Therefore, comprehending FMV is important for accurately reporting your taxable income and avoiding possible legal ramifications.

Stock Price Fluctuations

You need to understand that the potential financial gains from stock options are directly related to the company's stock price. This price can fluctuate due to a multitude of factors, including the company's financial performance, market conditions, and even global events. If the company's stock price falls below the exercise price, your options could end up 'underwater'. This means the exercise price is higher than the market price, which eliminates the financial benefit of exercising the options. Keeping a close watch on stock price movements is not just a matter of potential profit, but it can also be a legal necessity to ensure proper handling of your stock options and to avoid possible financial and legal implications.

It’s Complex, But That’s What Stock Options are About

Every individual's situation is unique. These considerations only provide a general overview of the complexities involved in stock option compensation, especially in the US. You should consult a financial advisor or tax advisor familiar with these matters to fully understand the implications and to make the most of your employee stock benefits. They can provide personalized advice based on your specific circumstances and tax bracket. As with all the points discussed so far, these emphasize the need for a sound understanding of all facets of stock options. 

However, in case your employer is yet to offer a good incentive, you may advocate instead for restricted stock units (RSUs). RSUs are way more flexible and transparent starting from issuance to vesting and liquidity. If you’re curious about how these plans work, book a demo with Upstock today.

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Casey Fenton

Founder, Upstock & Couchsurfing, AI and Equity Innovator

Casey Fenton, the founder of Upstock & Couchsurfing and an AI and equity innovator, has revolutionized how we perceive and implement equity in the workplace. His foresight in creating platforms that not only connect people but also align their interests towards communal and corporate prosperity has established him as a pivotal figure in technology and community building. Casey speaks worldwide on topics including ownership mindset, worker equity, With Upstock and Couchsurfing, he has demonstrated an unparalleled expertise in harnessing technology for the betterment of community interaction and organizational benefits.

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