Is ESPP Pre Tax? Understanding ESPP Taxation for Your Employee's Optimum Gains‍

Casey Fenton


January 4, 2024

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Remember the cautionary tale of Twitter employees who faced an unwelcome tax bill after the company went public in 2013? Some employees who had received equity compensation found themselves in a financial conundrum. In their excitement to cash in on the company's success, many sold their shares immediately, only to be shocked when tax season arrived. They learned the hard way that understanding when and how equity gains are taxed is crucial.

In a similar way, your employees could find themselves in the same boat if they're not well-informed about the tax implications of Employee Stock Purchase Plans (ESPPs). Don't let your team navigate this complex landscape blindly. As a startup founder or business owner, you have the power to equip them with the necessary knowledge to maximize their gains while minimizing their tax liabilities. That’s exactly what this comprehensive guide aims to provide: a roadmap to understanding ESPP taxation, so you can help your employees reap optimum benefits.

Is ESPP Pre Tax or Post Tax?

Let's get right to the point: ESPP contributions are generally made on a post-tax basis. This means the money your employees use to purchase company stock has already been subject to income tax. While pre-tax contributions would certainly offer a more immediate tax advantage, ESPPs usually do not offer this option. However, there are several ways to optimize tax liabilities on ESPP gains.

Understanding the Types of ESPPs

Before diving into the nitty-gritty of tax implications, it's vital to understand the two primary categories of ESPPs: Qualified and Non-Qualified. Each comes with its own set of rules, features, and, most importantly for this discussion, tax implications.

1. Qualified ESPPs: The Tax-Friendly Choice

Qualified ESPPs meet specific requirements laid out in Section 423 of the Internal Revenue Code. They're generally more tax-friendly and offer several advantages over their non-qualified counterparts:

  • Uniformity: One of the key requirements for a qualified plan is that it must be offered to all employees who meet certain broad-based eligibility criteria. This can create a sense of inclusivity within your company.

  • Discounts: Qualified ESPPs often come with the perk of purchasing shares at a discount, usually capped at 15%. This discount is not taxable upon purchase but will have tax implications upon sale, which we'll delve into later.

  • Look-Back Provision: Some qualified plans offer a 'look-back' provision, allowing employees to purchase stock at the lower of the price on either the offering date or purchase date. This could mean additional gains and more complicated but potentially favorable tax calculations.

2. Non-Qualified ESPPs: Flexibility at a Cost

Non-qualified ESPPs do not meet Section 423 criteria, and while they offer more flexibility in plan design, they come with less favorable tax treatment:

  • Selective Eligibility: You have the freedom to limit the plan to specific employees, such as executives or key contributors, without violating tax rules.

  • Variable Pricing: Non-qualified plans can have more variable pricing options for the stock, unlike qualified plans, which have restrictions on discounts and look-back provisions.

  • Immediate Taxation: Generally, any discount given in a non-qualified plan is considered ordinary income and is taxable at the time of purchase. While this immediate taxation can be a downside, it also means that there's a clearer, upfront understanding of the tax liability.

Understanding the type of ESPP you're offering or considering can significantly influence your employees' tax situations. Each type comes with a unique set of advantages and challenges that you should be fully aware of to help guide your employees toward sound financial decisions.

When Are Taxes Due on ESPPs?

In ESPPs, understanding when taxes are due can be as critical as knowing how much will be taxed. Ignorance of these timelines can lead to unwelcome surprises at tax time. There are specific dates and periods that dictate tax liabilities, and you'll want to mark these on your calendar, both as an employer and as an advisor to your employees.

1. Purchase Date

The purchase date, or the date the shares are bought, is the starting point for any future tax considerations. It's from this moment that various clocks start ticking.

Many ESPPs have an "offering period," which usually lasts around six months. During this time, money is deducted from employees' paychecks to buy shares at the end of the period. The date those shares are bought is the purchase date.

The purchase date is also the day when the countdown begins to determine whether the gains will be considered short-term or long-term, affecting the tax rate applied to those gains.

2. Sale Date

The sale date, or the date when the stock is sold, is when the tax liability is triggered:

  • Realization of Gains or Losses: On this date, any gains (or losses) are 'realized,' meaning they become subject to taxation. The tax implications will depend on whether these gains are short-term or long-term and whether your ESPP is qualified or non-qualified.

  • Reporting Requirements: After the sale date, it's critical to report the transaction on the tax return for that year. This involves a series of IRS forms, most commonly Form 8949 and Schedule D, which detail capital gains and losses.

3. The Holding Period

The period between the purchase date and the sale date is known as the holding period. This time interval can profoundly impact the kind of gains you have and their subsequent taxation.

If the holding period is one year or less, gains are considered short-term and taxed at ordinary income tax rates, which could be as high as 37%.

However, if the holding period exceeds one year, gains are considered long-term and qualify for the lower capital gains tax rate, which tops out at 20%.

Being aware of these key dates and periods is not just good practice; it's an essential part of strategic financial planning for both you and your employees. With this knowledge, you can better manage the tax impact of your ESPPs and advise your team on how to do the same.

Short-Term vs. Long-Term Gains

These categories determine the rate at which the gains will be taxed, and in turn, the net profit your employees will pocket. It's crucial to understand what constitutes short-term and long-term gains and the tax implications of each.

1. Short-Term Gains

Short-term gains result from selling shares within a year of the purchase date. The implications of this are straightforward but often costly.

Short-term gains are taxed at the individual’s ordinary income tax rate, which could be as high as 37% depending on their tax bracket.

While selling quickly might be tempting, especially if the stock price has increased substantially, the tax hit can be significant. Your employees should be fully aware that the quick turnover could mean less money in their pockets after taxes.

2. Long-Term Gains

Long-term gains are the profits made from selling shares held for more than a year. This holding period offers several advantages:

Long-term gains benefit from a more favorable tax rate, which can be as low as 0% and typically maxes out at 20%, depending on other income.

For qualified ESPPs, holding the stock for at least one year from the purchase date and two years from the offering date can result in even more favorable tax treatment, converting what would otherwise be ordinary income into capital gains.

The Interplay with Qualified and Non-Qualified Plans

It's essential to note that the nature of your ESPP—whether it's qualified or non-qualified—can interact with these categories of gains:

If your employees sell their shares immediately in a qualified plan, the discount they receive when purchasing the stock is treated as ordinary income, while any additional gains are considered capital gains. However, the most beneficial tax treatment comes from meeting the long-term holding requirements.

On the other hand, in non-qualified plans, the discount is treated as ordinary income at the time of purchase. Any additional gains (or losses) at the time of sale will be classified as either short-term or long-term capital gains, depending on the holding period.

Deductions and Credits: Any Room for Saving?

While the options are limited, there are a few avenues worth exploring to possibly reduce the tax burden for both you as the employer and your employees.

1. Employee Deductions

When it comes to individual tax deductions for employees participating in an ESPP, options are scarce. The IRS generally considers the purchase of company stock to be an investment, and thus, the costs related to the purchase usually can't be deducted:

2. No Pre-Tax Advantage

Unlike contributions to a 401(k) or an HSA, which can reduce taxable income, money used to purchase ESPP shares is already taxed as income. Therefore, there is usually no pre-tax advantage for ESPP participation.

3. Investment Expenses

Before the Tax Cuts and Jobs Act of 2017, employees could potentially deduct investment-related expenses. This is generally no longer the case, except for some very specific situations not applicable to most taxpayers.

4. Employer Deductions

As a business owner or startup founder, there are modest tax benefits on your end:

You can generally deduct the cost of employee compensation, including benefits, which may extend to ESPPs. However, this often doesn't result in a direct dollar-for-dollar tax benefit since ESPPs are usually funded through payroll deductions.

The costs associated with administering the ESPP can often be deducted as a business expense. This includes legal fees, accounting costs, and any third-party services used to manage the plan.

5. Tax Credits

In most cases, there are no tax credits available for participation in an ESPP. Tax credits are generally not designed to favor investment activities but rather to incentivize specific actions like education, homeownership, or energy efficiency.

While exceedingly rare, some states may offer tax incentives for participation in an ESPP. These are not common and usually require very specific conditions to be met.

Although options for deductions and credits related to ESPPs are limited, knowing what's available can help you and your employees make more informed decisions. While ESPPs might not offer the same level of pre-tax benefits as other employee benefits, understanding the full financial picture can help you strategize for optimal gains and minimal tax liabilities.

How to Optimize ESPP Tax Liabilities

Tax optimization strategies for ESPPs usually revolve around the timing of the sale. If your employees are in a lower tax bracket, it may be advantageous for them to realize gains sooner. Conversely, if they expect to be in a higher tax bracket in the future, holding the stock longer for capital gains treatment could be more beneficial.

Knowledge is Power

While ESPP contributions are not pre-tax, understanding the tax implications can help you guide your employees toward maximizing their gains. Ensure you are transparent about whether your ESPP is qualified or non-qualified and educate your staff on the importance of the purchase and sale dates. In doing so, you not only empower your team to make informed decisions but also contribute to their financial well-being, thereby fostering a happier, more committed workforce.

If you want a more flexible tax option for your equity compensation, try RSUs. At Upstock, we design this equity type to be flexible enough to account for tax liabilities and employee gains without hindering your own alignment goals. Book a demo with Upstock today to try.

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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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