Stock Options: A Guide to 1 of Tech’s Most Popular Incentives

You just got a bundle of stock options. Now we’re going to tell you what that means.
Lisa Bertagnoli
June 8, 2021
Updated: June 9, 2021
Lisa Bertagnoli
June 8, 2021
Updated: June 9, 2021

Tech entrepreneur Shariq Siddiqui loves stock options. As a tech employee, he’s reaped financial rewards from stock options offered to him as part of his compensation package. As an employer — he’s co-founder and CEO of Seattle-based contactless shopping startup Veeve — stock options help him entice talent to his new company and ensure that they stay on board for a few years. 

“If you’re going to build the next Google, Facebook or Slack, you have to focus on the best talent,” said Siddiqui. He’s not yet in the position to offer hundreds of thousands of dollars in salary to seasoned engineers, but he can offer new Veeve employees the chance to work hard to make Veeve a success, then cash in on that success. “Equity is the currency you use to negotiate,” he said. “It’s a competitive equity structure so the people working for you are completely vested and have the same goals as you do.”

A Stock Options Glossary

  • Stock option: A chance to buy equity in your company at a later date.
  • 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.

You as a tech employee might not have stock options now, but it’s a pretty sure bet you’ll be offered them at some point in your career. While tech didn’t invent stock options, 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’s a Stock Option?

“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. 


What’s a Strike Price?

Stock options come with a strike 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 lower 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.

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.


How Do Stock Options Make Money?

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.


What Are the Types of 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 units turned to cash when Uber had its initial public offering. “We joined at an opportune time,” said Vilardo. His 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.”

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Can I 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. 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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