How Stock Options Work as a Benefit


They are an opportunity for an employee to receive a future equity stake in a company through an option to purchase stock at a predetermined set price. Offering that chance to literally own a piece of the company motivates employees to work hard to make the company successful, and stay with the company so they can see their stock options turn into actual stock ownership.

Tech didn’t invent stock options. But it did make them popular as a recruiting and retention tool. In the early days of the internet, stock options provided a way for startups big on ideas but short on cash to attract employees, said Dan Sachs, executive director, education and programs at the University of Chicago’s Polsky Center for Entrepreneurship and Innovation. Companies offered hefty stock-option packages in lieu of hefty salaries, the idea being that as the company grew, its value — and the value of the stock options — would grow too.

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What Stock Options Are

“It’s an opportunity for an employee to receive a future equity stake in a company through an option to purchase stock at a predetermined set price,” said Sachs. Offering that equity stake, or chance to literally own a piece of the company, motivates employees to work hard to make the company successful, and stay with the company so they can see their stock options turn into actual stock ownership.

If stock options are part of your company’s compensation package, you’ll get them most likely three or six months after your start date. You’ll be asked to sign a legal document and set up an account at the company your employer uses for equity management.

For example, at Veeve, most of the 30 full-time employees have stock options. Veeve hires college graduates as interns for six to nine months, then conducts a performance review. Those hired as full-time employees receive a full compensation package of salary, stock options and a retirement savings plan.

Generally, you can’t exercise the options — meaning buy the stock — right away. The stock becomes yours to buy over time, which is called vesting. The longer you stay with the company, the more you are vested in the stock, meaning you have the option to buy a greater portion of the shares. The tech-industry standard is a four-year vesting period with a mechanism called a cliff. After a year, you’ll be 25 percent vested in your options, and then shares available to you to exercise pile up on a monthly basis.

Strike Price, Explained

Stock options come with a strike price (also called the grant price), which is the price at which you will buy your share. Because strike prices can change as a company grows, your options might have a different strike price than a colleague who started at the company two years before you or two years after you, because strike prices can change as a company grows.


  • Stock option: A chance to buy equity in your company at a later date.
  • Non-qualified stock option (NSO): Typically the type granted to full-time employees; they are taxed differently than incentive stock options.
  • Incentive stock option (ISO): The kind usually granted to vendors or outside consultants; they are subject to capital-gains taxes, while NSOs are not.
  • Option pool: The amount of stock your company’s founders set aside to use as incentives for employees.
  • Strike price: The price per share you are offered when you receive options; this is the price at which you will purchase them in the future.
  • Vesting: The process of, over time, making you eligible to exercise your stock options; in other words, purchase them.
  • Exercise: The act of purchasing your stock options; after the purchase, you actually own stock in the company.
  • Trigger: An event, say your company is acquired, that can automatically vest you in all of your options.

Which brings up a question. Who decides how much your company is worth? Companies hire independent appraisers to set a value for the company, much like houses are appraised, said Neil Tiwari, who’s in business development at Pulley, a San Francisco-based startup that manages equity plans for companies. The company is reappraised every so often as it matures and grows.

At its early stages, your company’s founders decide they will set aside a certain percentage of the stock (10 to 25 percent is customary) for employees. If a company grows quickly and that pool empties, the board can increase the size of the pool. However, “the consequence is that everyone else’s stock is diluted,” Tiwari said.

To Exercise or Not to Exercise?

Let’s say an employee has 500 shares, 25 percent of which are vested and available to exercise after one year of employment. This employee plans to stay at the company for the foreseeable future.

The benefit of not exercising the options until all are fully vested is that the employee will likely pay less taxes and receive more money, as the price of stock typically rises as time goes on, said Marlo Richardson, founder of Business Bullish, a website and resource that trains people in financial literacy and entrepreneurship.

“Outside of a dire emergency, I would recommend letting the stock become fully vested and then exercise the options when they are well above the strike price,” she said. “In a perfect scenario, roll the income into a qualified annuity and save more on the taxes.”

The employee described above might well wait for a triggering event — an acquisition or public stock offering that automatically vests all the options. “The benefit of not exercising at all is that the stock has the ability to increase in value and since it was a gift, at some point there is 100 percent gain as the result of any triggering event,” Richardson said.

On the flip side, “the drawback of not taking your money when it’s available is that you never know what’s going to happen that could trigger a market crash,” Richardson said. When events such as the 2008 market crash and the pandemic upend the market, “companies usually suffer, which means stocks as well,” she said.

How You Benefit From Stock Options

Your gamble, as an employee, is that the company’s value per share will be greater than the strike price. Say you’re offered 500 shares at a strike price of $5 per share. If the company is worth $20 a share when you exercise the options, you’re getting the stock at a 75 percent discount. If you sell the stock back to the company, or your company goes public or is acquired, you stand the chance to make money (taxes and capital gains must be accounted for) if the sell price or merger price per share is higher than that $5 strike price.

The big hope in tech is that the company you work for is acquired by a bigger organization in a cash or stock deal. Most of the time, your company’s equity plan includes a trigger, which is a financial event that would automatically vest you in all your shares, no matter where you are on the vesting timetable. For example, if your strike price is $5 a share and your company is acquired for $20 a share, you will realize $15 a share after taxes and capital gains, which will be different depending on your financial situation. (On the flip side, you can lose money if the price per share dips below your strike price.)

Absent a triggering event, you can buy shares as you become vested in them, or wait until you’re fully vested and purchase all of them at once. (Each approach has tax implications, so consult your accountant or financial adviser.)

You can also choose to not buy them. The caveat: Once you leave a company, you generally have 90 days to exercise your stock options (unless a longer period is part of a severance negotiation). After that, your options expire and you no longer have the chance to buy them.

If you do buy your options before leaving the company, you can hang on to them as you would any other investment.

Types of Stock Options

Companies grant two types of stock options: Incentive stock options, or ISOs, and non-qualified stock options, or NSOs. ISOs receive slightly more favorable tax treatment, said Tiwari. With ISO options, employees pay tax only when they sell the shares they have purchased. NSOs are often for contractors, advisors or other outsiders (meaning not employees) “looking for more skin in the game,” said Siddiqui of Veeve.

Companies also offer equity incentives via restricted stock units, or RSUs, and restricted stock awards, or RSAs. Employees own this stock from the day it is granted to them. With RSUs, employees must be vested (a year is standard); with RSAs, the employee owns them on the day they are granted.

Here’s how RSUs can work for tech-industry professionals. Michael Vilardo is co-founder and COO at Emile, a Los Angeles, California-based edtech startup focused on premium on-demand courses for high-school students. Prior to Emile, with a few gigs in between, Vilardo had been the fifth full-time employee at Dispatcher, a transportation and trucking company. Uber acquired Dispatcher in 2016 to help launch Uber Freight. Along with Dispatcher, Vilardo and his colleagues were “acqui-hired,” meaning that Uber retained them and their expertise post acquisition. Their compensation package included equity in Uber, which was then a privately held company.

On May 10, 2019, Vilardo’s restricted stock was recognized as income at Uber’s $45-per-share debut price. The resulting money, plus a full scholarship to earn an MBA, gave Vilardo the means to launch Emile. “Without those two, I would not be a full-time entrepreneur,” he said.

To pay it forward, literally and figuratively, Vilardo and his co-founders in Emile are offering stock options to their employees. “We want people to buy into our vision,” he said. “Everyone has incentives for the company to do well.”

Public Company Stock Options

Say your employer is already publicly traded, and you receive stock options. You’ll have the option to purchase a set number of shares at the strike price within a specific period. At the end of the vesting period, you’ll be able to purchase stock at the strike price, assuming that the stock’s fair-market price is not below the strike price, said Dylan O’Shea, a Merrill Lynch financial advisor based in New York City.

O’Shea adds that stock options can create “windfalls” that help people accomplish their financial goals. “We encourage developing a plan to assign the eventual sale proceeds to a specific goal, such as home renovations or purchase, saving for college or investing for retirement,” he said.

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When to Say ‘No’ to Stock Options

Stock options seem like a win-win: Founders can use them to woo high-level employees while retaining the cash that is so crucial to a startup. Employees gain early entry to a company that might be wildly successful, and the chance to learn more and do more than they would at a bigger, more established company, Siddiqui said.

So when would anyone ever turn down stock options? A few reasons. First, an employee is simply marking time at a company and has no faith in its ability to grow or isn’t sure how long she will be at the company.

“Stock options are sexy, but cash is cash,” said Dan Sachs of the Polsky Center. “If you don’t know where you’ll be three years from now, and you don’t want to be handcuffed to the company, then getting cash is a much better deal for you,” he said. Employees in that situation might negotiate for a higher salary in lieu of stock options.

O’Shea of Merrill Lynch also suggested finance-related questions that owners of stock options should ask themselves. Among them:

  • What happens to your options if you leave the company or it’s acquired?
  • Have you added your company’s blackout and trading rules into your personal cash flow calendar so you don’t need to make a poorly-timed financial decision to cover until the next window opens?
  • Have you discounted the value of the stock option by either the strike price or taxes? Or did you over-budget and set yourself up for an unfortunate surprise?
  • Do your options represent more than 10 percent of your net worth? If so, a major fall in share price could seriously and negatively affect your financial picture.

If you do accept stock options, then congratulations — and our fingers are crossed that your company is tech’s next newsmaker, ready to go public with a splash.

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