Get the Most Out of Employee Stock Options (2024)

Getting the most out of employee stock options means in part using them to your advantage come tax time. Over the years, employee stock options have become increasingly common to recruit higher-ranking employees and give them a sense of ownership in a company. According to the National Center for Employee Ownership, approximately 6,500 employee stock ownership plans cover 14 million participants.

Indeed, stock options, which give you the right to buy shares at a pre-determined price at a future date, can be a valuable component of your overall compensation package. But to get the most out of them, it’s essential to understand how they work and how they’re treated for tax purposes.

Key Takeaways

  • Employee stock options can be a lucrative part of a compensation package, although not every company offers them.
  • Workers can buy shares at a pre-determined price at a future date, regardless of the price of the stock when the options are exercised.
  • Non-qualified stock options (NSOs) are granted to employees, advisors, and consultants.
  • With NSOs, you pay ordinary income taxes when you exercise the options, and capital gains taxes when you sell the shares.
  • Incentive stock options (ISOs) are only for employees.
  • With ISOs, you only pay taxes when you sell the shares, either ordinary income or capital gains, depending on how long you held the shares first.

How Employee Stock Options Work

Stock options are often offered as an employee benefit. The major advantage of a stock option is the ability to buy shares in the future at a fixed price, even if the market value is higher than that amount when you make your purchase. Your ability to exercise your options is determined by a vesting schedule, which lists the number of shares an employee can purchase on specific dates.

For example, an employer may grant you 1,000 shares on the grant date, with 250 shares vesting one year later. That means you have the right to exercise 250 of the 1,000 shares initially granted. The year after, another 250 shares are vested, and so on. The vesting schedule also includes anexpiration date. That's when the employee no longer has the right to purchase company stock under the terms of the agreement.

The price at which the employee can purchase shares is known as theexerciseprice. In most cases, it's simply the stock's market value on the grant date.

Note

If the stock price goes up by the time you vest, your option is considered "in the money," meaning you can buy the shares at a lower price than they're now worth.

Get the Most Out of Employee Stock Options (1)

NSO vs. ISO

There are two main types of employee stock options—non-qualified stock options (NSOs) and incentive stock options (ISOs). One difference between them is eligibility. Companies can grant the former to employees, consultants, and advisors. However, only employees can receive ISOs. But the biggest distinction is how they’re treated for tax purposes at the exercise date.

Non-qualified stock options (NSOs)

In the case of an NSO, you incur a bill right when you exercise the option. The difference between the exercise price and the fair market value of the shares is subject to ordinary income taxes in that year.

Let’s say you have options with an exercise price of $10 a share that rose to $30 by the time you exercised them. You’d pay income taxes on $20 per share.

Any further increase in the sale price is subject to the more favorable capital gains rate. which is typically no more than 15% for individuals, when you subsequently sell the shares.Suppose they rose in value to $55 a share when you sold them two years later. You’d pay the long-term capital gains rate on $25 per share (though you’d pay the higher short-term rate if you sold them within a year of their purchase).

Incentive stock options (ISOs)

ISOs are usually seen as more advantageous for the employee because the exercise date isn’t a taxable event. Even though higher-earning employees have to make an alternative minimum tax (AMT) adjustment based on the difference between the current market price and the exercise price.

Instead, you settle up with the IRS when you actually sell your shares down the road. If you’ve held the stock for more than a year, you’ll incur the long-term capital gains tax on the difference between the exercise price and the eventual sale price.So if we use the same prices in the earlier example, you’d pay the capital gains tax of $45 per share ($55 sale price minus the $10 exercise price).

To get the preferred tax treatment, ISOs must be held for two years from the date they are granted and at least one year from the exercise date. Otherwise, a “disqualifying disposition” occurs, and the difference between the grant price and market value on the exercise date is subject to ordinary income tax.

Get the Most Out of Employee Stock Options (2)

Mind the Expiration Date

Stock options don’t last forever. Typically, there’s a vesting schedule that lasts anywhere from one to four years, though some employees may have up to 10 years.And if you leave the company for whatever reason, whether it’s because of a layoff, resignation, or retirement, you may only have 90 days to use them.

If you have in-the-money options at your disposal, you should act well before the expiration date. Some employees forget about the deadline or wait on their decisions as long as possible, hoping that the price will go up higher still. That strategy can backfire, however.

If you’re within a few weeks of the expiration and the stock is trading above the exercise price. The last thing you want to do is let the options expire and be worthless.

Special Considerations

A generous stock option benefit is certainly nothing to complain about. But it does have a significant risk—the possibility that too much of your wealth will be tied up in a single stock.

As a general rule, you want to avoid having more than 10% to 15% of your portfolio tied to a specific company.Should the organization fall on hard times, you would not be diversified enough to cushion the blow.

If you’re crossing that threshold, you might think about selling enough stock each year to keep your nest egg safe from excess volatility risk. To account for fluctuations in the market, consider dividing the sale into a series of transactions over a few weeks or months, especially for larger amounts.You can then use that income to increase your 401(k) and IRA contributions.

What Are Employee Stock Options?

Employee stock options area benefit offered by some companies as part of their compensation package. The options allow the employee to purchase company stock for a period of time, at a reduced rate.

Do You Have to Pay Taxes on Employee Stock Options?

Like any stock, you will have to report the deductible loss or taxable income when you sell the stock you bought, treating it as a capital loss or gain, and any income you earn from the stock will be treated as ordinary income, according to the Internal Revenue Service.

What Are 2 Types of Employee Stock Options?

Two main types of employee stock options are non-qualified stock options (NSO) and incentive stock options (ISO). If you are a former employee, freelancer, consultant, or advisor, a company can offer you an NSO, even if you are no longer working for the company. An ISO is only available to employees.

The Bottom Line

Employee stock options can be a valuable part of your compensation package, especially if you work for a company whose stock has been soaring of late. In order to take full advantage, make sure you exercise your rights before they expire. When you retire, stock options can be highly beneficial, so make sure to take advantage of this benefit if offered to you, but make sure you understand the tax effect of your decisions.

Get the Most Out of Employee Stock Options (2024)

FAQs

What is the best thing to do with stock options? ›

Hold Your Stock Options

If you believe the stock price will rise over time, you can take advantage of the long-term nature of the option and wait to exercise them until the market price of the issuer stock exceeds your grant price and you feel that you are ready to exercise your stock options.

When should I sell my employee stock options? ›

Exercise and/or Sell As Soon As Possible

Many companies issue stock compensation with a schedule that's tied to a period of time you must remain with the company in order to receive the value of the plan benefit. Your first opportunity to take action is often whenever your stock options or grants are fully vested.

Is it worth it to buy employee stock options? ›

Employee stock options can be a valuable part of your compensation package, especially if you work for a company whose stock has been soaring of late.

When should you exercise your ESOPs? ›

Exercise period: This crucial timeframe is predetermined in the ESOP agreement and specifies when options can be converted into shares. Vesting requirements: Before exercising, options must be vested, meaning the employee has completed the required service period.

What is the easiest stock option strategy? ›

Buying Calls Or “Long Call”

Buying calls is a great options trading strategy for beginners and investors who are confident in the prices of a particular stock, ETF, or index. Buying calls allows investors to take advantage of rising stock prices, as long as they sell before the options expire.

Can you live off of stock options? ›

It's realistic for an options trader to make at least $100,000 per year or more full-time, but it's important to realize that most traders won't make this amount. It takes hard work, mental discipline, and proper capital for a trader to make this kind of money.

Is it better to exercise an option or sell it? ›

Often it is more profitable to sell the option than to exercise it if it still has time value. If an option is in the money and close to expiring, it may be a good idea to exercise it. Options that are out-of-the-money don't have any intrinsic value, they only have time value.

What is the average employee stock option? ›

Size of the option pool

A good starting point when thinking about option allocations, is to consider the total sizeof the option pool. A typical employee stock option pool at pre-seed round is about 12-15%, diluted to 10% at series A.

What happens if I don't exercise my stock options? ›

Because if you don't exercise your options before the expiration date, they will be worth absolutely nothing. Nada. Zip. Options are very much a use-it-or-lose-it proposition, and it could be very painful to “lose it” if your strike price is below the current fair market value of the common stock.

What are the downsides of employee stock options? ›

Dilution can be very costly to shareholder over the long run. Stock options are difficult to value. Stock options can result in high levels of compensation of executives for mediocre business results. An individual employee must rely on the collective output their co-workers and management in order to receive a bonus.

Should I max out my ESPP? ›

If you have no debt, you're contributing up to the company match in your 401(k) PLUS saving money, you should do what you can to max out contributions to both your 401(k) plans and your ESPP. This will result in you substantially growing your net worth.

Do you pay taxes twice on stock options? ›

Stock options are typically taxed at two points in time: first when they are exercised (purchased) and again when they're sold. You can unlock certain tax advantages by learning the differences between ISOs and NSOs.

Who benefits from ESOPs the most? ›

The Benefits To Employees

The ESOP is generally designed to benefit employees who remain with the employer the longest and contribute most to the employer's success. Since stock is allocated to each employee's account based on a contribution by the company, the employee bears no cost for this benefit.

Should you exercise stock options immediately? ›

In many cases it can be advantageous to exercise your stock options early (provided you have the cash, and assuming you believe in the company given you accepted a job there). The first benefit of exercising early is that you will likely have zero (or very little) tax liability at the time of exercise.

Do you have to pay taxes when you exercise stock options? ›

You have taxable income or deductible loss when you sell the stock you bought by exercising the option. You generally treat this amount as a capital gain or loss. However, if you don't meet special holding period requirements, you'll have to treat income from the sale as ordinary income.

How do I make money on stock options? ›

Options traders can profit by being option buyers or option writers. Options allow for potential profit during volatile times, regardless of which direction the market is moving. This is possible because options can be traded in anticipation of market appreciation or depreciation.

Should you cash out stock options? ›

If you exercise your options at the right time, you could make valuable contributions to all of the above. The sooner you realize that cashing in your stock is not equivalent to betraying your company, the sooner you can start making smart decisions about your money.

Are stock options a good way to make money? ›

Options can be a better choice when you want to limit risk to a certain amount. Options can allow you to earn a stock-like return while investing less money, so they can be a way to limit your risk within certain bounds. Options can be a useful strategy when you're an advanced investor.

What not to do when trading options? ›

If you want to trade options, be sure to avoid these common mistakes.
  1. Not having a trading strategy. ...
  2. Lack of diversification. ...
  3. Lack of discipline. ...
  4. Using margin to buy options. ...
  5. Focusing on illiquid options. ...
  6. Failing to understand technical indicators. ...
  7. Not accounting for volatility. ...
  8. Bottom line.
Feb 5, 2024

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