Many employers offer an employee stock purchase plan, or ESPP, to allow employees to purchase company stock with ease. As an incentive to participate, many ESPPs allow you to purchase stock at a discount from the current market price.
Each ESPP comes with its own specific set of rules, but that discount can be as much as 15%. That makes the argument for participating in this kind of plan pretty strong – but that doesn’t mean you should always participate.
Prior to determining if you should participate or not, you should have a thorough understanding of your plan’s rules and benefits. Read your plan document and ask HR if you have any questions – or work with a financial advisor who can help you sort through the details.
Assuming it does make sense to participate in your plan, you should then consider how to best optimize your plan’s benefits. In this article, we’ll walk through several strategies that you could use when participating in (and eventually selling stock from) an employee stock purchase plan.
An Introduction to Your Employee Stock Purchase Plan
Generally speaking, your plan will follow the following process (again, consult your plan document for specific rules pertaining to your plan):
Your company establishes an ESPP and sets an offering date and offering period. The offering date is the date the plan starts and the offering period is how long from the offering date you can purchase shares. The purchase date is the date when your company buys shares.
- You enroll in the ESPP by electing to defer a percentage of income or dollar amount from your paycheck into the plan (subject to certain limits set by the plan document or an annual IRS limit of $25,000).
At predetermined intervals set by the plan, the ESPP uses your deferred dollars to buy shares of company stock. The price you pay for your shares via the ESPP is the lower of either the fair market value on the offer date or the fair market value on the purchase date.
- If you plan offers a discount from the purchase price, that discount will be applied to the price paid.
Often, you’ll find the offer date and the purchase date are 6 months apart. During this 6-month period, the ESPP collects your deferred dollars. Then, at the end of the 6-month period, the ESPP buys the shares at the lower of the two prices.
Essentially, your ESPP gives you the chance to have a free look at your stock over a 6-month period, with no investment risk. However, this doesn’t mean you don’t need to pay attention.
Your ESPP gives you the opportunity to buy shares at a great price. But once the shares are purchased, you are subject to the normal risk of owning stock, and you should have a strategy in place to manage that risk.
The Strategies You Should Know for Your Employee Stock Purchase Plan
The exercise strategies for an employee stock purchase plan can be simplified into two options:
- Selling your shares as soon as possible.
- Holding your shares for a specific time period.
Choosing one of these two strategies isn’t quite as simple, though. Depending how when and how your sell your shares, there may be different things to consider regarding income tax, investment risk, and concentrated equity – all of which should influence which option you choose.
Let’s explore in a bit more detail.
Option 1: Sell Your ESPP Shares as Soon as Possible
You could make the argument that selling ASAP is always the best strategy because selling your shares immediately allows you to capture any immediate gain thanks to the fact you bought at a discount but can sell at market value.
For example, let’s assume that your company shares are currently trading at $100 per share and the company offers a 15% discount. If you choose to sell right away, you buy shares for $85 and sell for $100. That’s an immediate gain of $15 per share, just because you got to buy at a discount.
The thought behind an immediate sell may be to capture your value immediately and eliminate the potential for loss via a falling stock price. There is typically no consideration for holding the stock any longer than necessary, no consideration for income tax planning, and no consideration to an appreciating stock price.
The beauty of this an immediate sell of your ESPP is that there is very little risk when you participate. But be sure to check with your plan document before deciding to run with this strategy. Not all ESPPs allow you to sell your shares immediately after purchase.
Assuming you can sell ASAP, let’s look at the possible outcomes of using your ESPP this way in three different markets.
|Offer Date Price||$100.00||$100.00||$100.00|
|Purchase Date Price||$150.00||$100.00||$50.00|
|Final Sale Price||$150.00||$100.00||$50.00|
|Ordinary Income (33%)||$21.45||$4.95||$2.48|
|After Tax Gain||$43.55||$10.05||$5.03|
|After Tax Proceeds||$128.55||$95.05||$47.53|
In this example, scenario 1 produces the highest after tax gain. Much of this gain is due to the purchase rules of an ESPP.
If you were able to purchase your shares at the better of the purchase date price and the offer date price. This means you can purchase shares via the ESPP at $100, when the current market price (the purchase date price) is $150. (This is a visual example of the value of the “look-back” provision.) On top of all that you get a 15% discount from the $100 offer date price.
Even more eye-opening may be the outcome for scenario 3, when the purchase date price is lower than the offer date price. In this scenario, you purchase the shares at the lower of the offer date price of $100 and the purchase date price of $50, less the 15% discounts.
The fact that you can purchase shares at the better of the two prices means that you are protected from a down market during the offering period. If the price goes down, you know you will buy the shares at the lowest price. As the example shows, even in a down market you can buy the shares for $42.50 (purchase date price less a discount) and immediately sell them for $50.
Other Thoughts on Selling Your ESPP Shares Immediately
It’s easy to understand why an employee stock purchase plan can be a great deal for employees. Some people argue that it’s a no-brainer.
But in practice, it can be difficult to remain diligent in implementing your personal strategy to sell. Whether out of guilt for selling company stock, not being “part of the team,” or simply laziness at worst or forgetfulness at best, there are many reasons why someone may not follow through on their goal to sell.
It’s often this risk that gets people into trouble, as holding onto company stock that falls in value could cost you a lot of money.
Option 2: Holding Employee Stock Purchase Plan Stock for a Period of Time
If you elect to hold your employee stock purchase plan shares beyond the point of option 1 — in other words, doing anything but selling immediately — you need to consider market volatility, tax, concentrated equity, and other financial planning issues.
You also should know the difference between a qualifying and disqualifying disposition. If you meet the standard for a qualifying disposition, a portion of the gain (if any) may be subject to preferential long-term capital gains treatment.
A qualifying disposition of ESPP shares is anything that meets the following standards:
- The stock must be held for at least 1 year past the original purchase date
- The stock must be held for at least 2 years after the original offer date
Anything that is not a qualifying disposition is a disqualifying disposition. A disqualifying disposition means all gain will be subject to ordinary income tax rates.
The preferential tax treatment of the qualifying disposition comes with a risk: holding potentially volatile company stock. It’s possible that during the time you hold the stock, the stock price could go down and any or all value could be wiped out, including what you paid for the stock (to be fair, it’s also possible that the stock price could go up).
If we make an assumption that the stock does not move and that you hold the stock long enough to make the transaction eligible for a qualifying disposition, here are some potential outcomes across various types of markets:
|Purchase Date Price||$150.00||$100.00||$50.00|
|Final Sale Price||$150.00||$100.00||$50.00|
|Ordinary Income (33%)||$4.95||$4.95||$2.48|
|Capital Gains (15%)||$7.50||$0.00||$0.00|
|After Tax Gain||$52.55||$10.05||$5.03|
|After Tax Proceeds||$137.55||$95.05||$47.53|
The after-tax proceeds of a qualifying disposition, assuming a flat stock price in scenario 2, equals 95.05. This is an identical outcome to scenario 2 in the “sell immediately” scenario.
If we evaluate scenario 1, the after-tax proceeds of a qualifying disposition of employees stock purchase plans shares is $137.55. Comparing this to the “sell immediately” scenario 1 of $128.55, there’s an additional value of $9 per share.
You may want to ask yourself if $9 per share, or approximately 7% more, worth the risk of holding your company stock for at least one more year. Holding the stock for the sole purpose of paying less tax may not be worth the risk of actually holding the stock and having the value potentially drop.
What Does This Tell Us About Employee Stock Purchase Plans?
If you are simply looking to make money, the immediate sale of your employee stock purchase plan shares may be a great idea. It’s possible to use your ESPP to create additional wealth with little to no risk by doing so.
As you hold your stock longer in an attempt to pay a better tax rate, you may be taking risk that might not be worth the corresponding payoff. By holding the company stock, you may participate in the possible upside of the market. However, you should balance upside opportunity with downside risk.
The potential tax benefit of a qualifying disposition, as illustrated by the simple example above, is a “nice to have.” It should not be the sole reason or justification to hold your shares.
Your ESPP is a great way to create wealth, if you plan accordingly and execute that plan well. That plan should consider the risk you are willing to take with your employee stock purchase plan and how company shares fit into your overall financial plan.
Tax services are not offered through, or supervised by Lincoln Investment, or Capital Analysts.
None of the information in this document should be considered as tax advice. You should consult your tax advisor for information concerning your individual situation.
Projections or other information regarding the likelihood of various investment outcomes are hypothetical in nature, do not reflect actual investment results and are not guarantees of future results.
A plan of regular investing does not assure a profit or protect against loss in a declining market. You should consider your financial ability to continue your purchases over an extended period of time.