Stock Purchase Plan: FAQs Answered for Employees with ESPPs‍

Stock Purchase Plan: FAQs Answered for Employees with ESPPs‍

June 19, 2023

Stock Purchase Plan: FAQs Answered for Employees with ESPPs‍

Picture this: You're a dedicated employee, sitting at your desk when a colleague bursts into the room with an infectious grin. They've just sold their Employee Stock Purchase Plan (ESPP) shares, pocketing a substantial profit. As you watch them celebrate, you can't help but wonder: 'What's the secret to their success?' This scenario plays out in workplaces across the country, where employees seize the opportunity to become shareholders in their own companies and reap the rewards.

But it's not just about celebrating a windfall. Understanding ESPPs is like unlocking a financial superpower that can help you build wealth, secure your future, and achieve your dreams. In this comprehensive guide, you’ll uncover the complexities of ESPPs, answering all your burning questions so you can make smart financial decisions and potentially turn your workplace enthusiasm into a thriving investment opportunity.

What is An Employee Stock Purchase Plan?

An Employee Stock Purchase Plan (ESPP) is a benefit offered by many employers to their employees. It allows you to purchase company stock at a discounted price, typically through payroll deductions. The primary goal of an ESPP is to encourage employee ownership in the company, aligning the interests of employees with those of shareholders.

Who is Eligible for a Stock Purchase Plan?

Eligibility for an Employee Stock Purchase Plan (ESPP) is a critical factor that determines your ability to participate and leverage this valuable financial benefit. Each company's ESPP comes with its own set of eligibility criteria, and understanding them is the first step towards maximizing the advantages it offers. So who qualifies for ESPPs?

1. Employment Status

Most ESPPs are designed for active employees, both full-time and part-time, who work directly for the company offering the plan. While this encompasses a significant portion of the workforce, it's essential to note that some ESPPs may extend eligibility to other employment types, such as contractors or consultants. Understanding your specific employment status is crucial to determine if you can participate in your company's ESPP.

2. Length of Service

Some employers require a minimum length of service before employees become eligible to participate in the ESPP. This criterion aims to encourage long-term commitment to the organization. The waiting period can vary, so carefully review your company's ESPP guidelines to know when you'll become eligible.

3. Geographic Restrictions

In certain cases, ESPP eligibility may be restricted to employees in specific geographic regions or countries where the company operates. This restriction is often related to legal and regulatory considerations in different regions. If your company has a global presence, verify if you qualify based on your location.

4. Participation Date

Your eligibility might also be tied to specific participation dates or enrollment periods. Companies typically announce these periods when employees can enroll in the ESPP or make changes to their contributions. Missing these dates could mean having to wait for the next enrollment period to join the plan.

5. Minimum Working Hours

Some ESPPs require employees to meet a minimum number of working hours per week or month to be eligible. This criterion is typically used to distinguish between part-time and full-time employees and to ensure that part-time employees can participate without overburdening the plan.

6. Job Classification

In certain cases, ESPP eligibility may be linked to job classifications or levels within the company. For example, only employees in management positions or specific job roles may be eligible. Understanding how your job classification affects your eligibility is crucial.

7. Union Membership

If your workplace has a union, ESPP eligibility may be influenced by union agreements. This means that union members could have different eligibility criteria or participation terms than non-union employees. Be sure to check with your HR department or union representatives for clarification.

What's the Difference Between Qualified and Non-Qualified ESPP?

Understanding the distinction between qualified and non-qualified Employee Stock Purchase Plans (ESPPs) is crucial because it has a significant impact on how your participation is taxed and the financial benefits you can reap. Here's how these two categories differ:

  • Tax Treatment: The most substantial difference between qualified and non-qualified ESPPs lies in their tax treatment. In a qualified ESPP, if you meet specific IRS requirements, the discount you receive when purchasing company stock is generally taxed as long-term capital gains. This often results in a lower tax rate compared to ordinary income tax. On the other hand, non-qualified ESPPs typically tax the discount as ordinary income, subject to your regular income tax rate. This disparity in tax treatment is a crucial factor to consider when deciding which type of ESPP you have or want to participate in.

  • Participation Limits: Qualified ESPPs are subject to specific participation limits set by the IRS. The maximum allowable contribution per calendar year is capped at $25,000, or a lower limit defined by your company's plan. Non-qualified ESPPs, however, do not face these IRS-imposed contribution limits. If you seek to invest more substantial amounts in your ESPP, a non-qualified plan may be a more suitable option.

  • Holding Period Requirements: Qualified ESPPs often have holding period requirements to enjoy favorable tax treatment. Generally, you must hold the purchased stock for at least two years from the start of the offering period and one year from the purchase date. Non-qualified ESPPs typically do not have such holding requirements. Understanding these holding period rules is essential for planning your stock sales and managing tax implications.

  • Availability to All Employees: Non-qualified ESPPs may have more flexibility in terms of which employees can participate. While qualified ESPPs often have stringent rules about who can join, non-qualified plans may extend eligibility to a broader range of employees, including highly compensated employees and key executives.

  • Administrative Complexity: Qualified ESPPs tend to be more administratively complex due to IRS regulations. Companies offering qualified plans must adhere to specific rules regarding enrollment, contribution limits, and reporting. Non-qualified ESPPs may offer a simpler administrative process.

  • Employer Deductions: For the company offering the ESPP, there are differences in tax deductions. Qualified ESPPs may offer employers tax benefits, such as deductions for the discount offered to employees. Non-qualified ESPPs may not provide the same tax advantages for the company.

How Does an ESPP Work?

Understanding how an ESPP works is crucial to making the most of this benefit. Here's a step-by-step overview:

1. Enrollment and Contribution Percentage

ESPP participation usually begins with an enrollment period, during which you can choose to join the plan. Once enrolled, you'll specify the percentage of your salary that you want to contribute to the ESPP. This amount is deducted from your paycheck after taxes, creating a convenient and automatic savings mechanism.

2. Accumulation Period

After enrollment, ESPPs typically have defined accumulation periods, often lasting six months or a year. During this time, your contributions accumulate in an ESPP account. The funds are set aside, ready to be used to purchase company stock at a later date.

3. Stock Purchase Date

At the end of the accumulation period, the accumulated contributions are used to purchase company stock on the designated stock purchase date. The purchase date is usually at the end of the accumulation period.

4. Discounted Purchase

One of the primary benefits of ESPPs is the opportunity to buy company stock at a discount. The purchase price is typically set at around 85-90% of the fair market value of the stock on the purchase date. This discount can represent substantial savings and is a key incentive for employees to participate.

5. Stock Acquisition

After the purchase is made, the acquired shares are deposited into your brokerage account. These shares are now yours to manage as you see fit, and they can form a valuable part of your investment portfolio.

6. Hold or Sell

At this point, you have a crucial decision to make. You can choose to hold onto the purchased shares, allowing them to potentially appreciate over time, or you can decide to sell them. The decision may depend on your financial goals, market conditions, and personal investment strategy.

7. Tax Implications

The tax treatment of your ESPP shares varies depending on whether your plan is qualified or non-qualified. Qualified plans often come with favorable tax benefits, but they may require you to meet specific holding requirements to realize these advantages. Non-qualified plans may have less favorable tax treatment but offer more flexibility.

8. Repeat the Cycle

ESPPs typically operate on a cycle, with multiple accumulation periods throughout the year. This means you can continue to participate and build your investment in company stock over time.

What is An ESPP Lookback?

An ESPP lookback feature can be a valuable addition to your plan. It allows you to purchase company stock at a discount based on the lower of two prices: the stock price at the beginning or the end of the purchase period. Here's how it works:

Let's say the stock price at the start of the purchase period is $50, and at the end, it's $60. Without the lookback feature, you would purchase the stock at a 15% discount off the market price, which would be $60 - 15% = $51.

However, with the lookback feature, you get to purchase the stock at a 15% discount off the lower of the two prices. So, you'd buy it for $50 - 15% = $42.50. This can result in more significant savings for you, making the ESPP even more attractive.

How Are ESPP Stocks Taxed?

The taxation of ESPP stocks depends on whether your plan is qualified or non-qualified:

  • Qualified ESPP: The tax benefits are substantial. If you meet specific holding requirements (usually holding the stock for at least two years from the start of the offering period and at least one year from the purchase date), the discount you received when purchasing the stock is generally taxed as long-term capital gains, which often have a lower tax rate than ordinary income.

  • Non-Qualified ESPP: The discount on the stock you receive through a non-qualified ESPP is typically considered ordinary income and is subject to income tax at your regular tax rate. Any gains made when selling the stock are also taxed as either short-term or long-term capital gains, depending on how long you hold the stock.

When is the Best Time to Sell ESPP Stocks?

The ideal time to sell your ESPP stocks depends on your financial goals, the market conditions, and your tax strategy. Here are some key considerations:

1. Holding Period

If you have a qualified ESPP, consider holding the stock for at least the required holding period to take advantage of the favorable tax treatment on the discount.

2. Diversification

Evaluate your overall investment portfolio. Selling ESPP stocks can help you diversify your investments and reduce exposure to a single company's stock.

3. Market Conditions

Keep an eye on the stock's performance and the broader market. Selling when the stock is performing well or when you need the funds may be a good strategy.

4. Tax Planning

Consult with a tax advisor to determine the tax implications of selling your ESPP stocks and how they fit into your overall tax strategy.

5. Financial Goals

Consider your short-term and long-term financial goals. Selling ESPP stocks can provide funds for various purposes, such as buying a home, paying off debt, or saving for retirement.

Remember that there's no one-size-fits-all answer to the best time to sell ESPP stocks. It's a decision that should align with your unique financial situation and objectives.

Why RSUs Could Be A Better Stock Investment for Employees

While ESPPs offer an attractive opportunity to purchase company stock at a discount, Restricted Stock Units (RSUs) are another investment option you should consider. Here's why RSUs might be a better choice for some employees:

✔ No Out-of-Pocket Expense: Unlike ESPPs, RSUs don't require you to contribute your own money to acquire shares. Your employer grants you RSUs as part of your compensation package.

✔ Immediate Ownership: RSUs grant you ownership of company stock immediately upon vesting, typically over a predetermined time frame.

✔ No Purchase Decision: With RSUs, you don't have to decide when to buy stock or worry about market volatility. You receive shares as they vest.

✔ Tax Simplicity: RSUs are usually taxed as ordinary income when they vest, making the tax treatment more straightforward compared to ESPPs.

✔ Long-Term Focus: RSUs often come with vesting schedules that encourage employees to stay with the company for the long term, aligning your interests with the company's success.

However, it's essential to recognize that RSUs may not offer the same immediate financial benefits as ESPPs in terms of discounts and tax advantages. Your decision between ESPPs and RSUs should align with your financial goals, risk tolerance, and investment strategy.


Employee Stock Purchase Plans (ESPPs) can be a valuable financial benefit, allowing you to become a shareholder in your company while enjoying discounts and potential tax advantages. Understanding the eligibility criteria, tax implications, and strategic considerations will help you make the most of this benefit. 

Additionally, considering alternative stock investments like Restricted Stock Units (RSUs) can further diversify your portfolio and align with your long-term financial goals. Be sure to consult with a financial advisor to tailor your investment strategy to your unique circumstances. By making informed choices, you can make the most of your ESPP and build a stronger financial future.

For more info on other types of equity compensation that your company might be offering, feel free to browse Upstock’s blog on RSUs, stock options, ESPPs, and RTUs. Alternatively, you may explore its learning materials to see how RSUs stack up against popular equity structures.

Unlock Your Equity IQ: Are You an Upstock Pro Yet?