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How to Maximize Your Cisco Employee Stock Purchase Plan (ESPP)

If you work for Cisco Systems or another company offering an Employee Stock Purchase Plan (ESPP), it’s essential to understand how to maximize this valuable employee benefit. If used effectively, an ESPP can be a powerful tool for building wealth.

In this post, we’ll cover:

  1. An overview of the Cisco ESPP.
  2. Strategies for maximizing the investment value of your ESPP.
  3. Tax implications of participating in the ESPP.

An ESPP lets you purchase company stock at a discount, offering a potential financial boost that’s designed to encourage both employee performance and retention. Let’s explore how the Cisco ESPP works, including some specific strategies for maximizing its benefits.

Timing & Enrollment in Cisco’s ESPP

As a Cisco employee, you can participate in the ESPP if you work at least 20 hours per week for a minimum of five months per year. Cisco’s ESPP features consecutive, overlapping 24-month offering periods, with four purchase periods (each six months long).

Here’s what to keep in mind about enrollment:

Enrollment Deadline: Make sure to enroll by the deadline specified by your plan administrator.

Contribution: You can elect to contribute up to 10% of your “Eligible Earnings” to the ESPP, with a maximum of $25,000 per year, deducted directly from your paycheck after taxes.

Recommendation: If possible, maximize your contribution to make the most of this benefit.

How the Cisco ESPP Works

After enrolling in the ESPP and choosing your deferral amount, your contributions will be drafted from your pay over the duration of the purchase period.

At the beginning of the offering period, the stock price of CSCO will be established and recorded. For example, if the offering period started on July 1, 2022 the price of Cisco Systems Inc. stock (CSCO) would be recorded as $42.60.

Your deferrals into the plan will continue through purchase period. These deferrals are put in an account managed by the ESPP plan administrator until the purchase date.

The money you've deferred to the ESPP throughout the purchase period will now be used to buy CSCO stock at a 15% discount from the stock’s closing price on the purchase day. In this example, if Cisco stock closes at $48 on December 30th (purchase date), your ESPP contributions will be used to purchase the stock at $40.80... 15% lower than the current share price.

There’s a Wrinkle: The Cisco ESPP Look Back Provision

Cisco’s ESPP has an additional provision that benefits participants, called a “look back” provision. If the price at the beginning of the purchase period is lower than the stock price at the end of the purchase period, you'll purchase the stock at a 15% discount from the lower price at the beginning of the period. In this example, you would acquire CSCO at $36.21 which is more 23% discount from its current market share price of $48!

And Another One: Withdraw During the Offering Period

Another feature of the Cisco ESPP is the ability to opt out of an offering period and re-enroll in the next offering period when the time comes. For example: you enroll in the January 2021 ESPP offering period but decide to withdraw before the 2-year offering period expires, and you instead re-enroll in the very next offering period starting January 2022.

When you withdraw from an offering period, you can elect to either finish out the current purchase period or get your accumulated contributions back in cash.

Understanding the Tax Treatment for ESPP

You’ll owe tax on your ESPP investment. The amount of tax is determined by several factors including your household income, the "holding period" of your investment (compared to the purchase date and offering date), the market price of the stock on purchase date and sell date, and your discounted purchase price.

There are two holding periods that are important for Cisco ESPP plan participants:

  1. A 1 year holding period commencing on the purchase date(s).
  2. A 2-year holding period commencing on the offering date.

If you satisfy the first holding period (hold the shares 1 year after the purchase date) you will pay long term capital gains tax on any growth over your purchase price of the stock on the offering date and the stock price on the day you sell.

If you satisfy the second holding period (hold the shares 2 years from the beginning date of the offering period) you will only pay ordinary income tax on the difference between the stock price on the offering date and your discounted purchase price, this is known as a qualified dispostion. Let's look at two examples using the following fact set:

Stock Price on Offering Date: $42.60

Stock Price on Purchase Date: $47.94 

Stock Price on Sale Date: $55.60

Look Back Discount Price: $36.21

What is a Qualified Disposition? 

Here's an example with some numbers.

Example: Allison invests $14,194 into her ESPP during purchase period 1. The offering price on July 1, 2022 was $42.60 and the price of the stock on the purchase date (12/30/22) is $47.94. Allison buy shares at $36.21 which represents a 15% discount from the look back price (offering date price) of $42.60.

Her $14,194 investment allows her to purchase 392 shares. She decides to hold the shares until September 22, 2024 and sell the shares for $55.60 (the current market price). She has held the shares 1 year past the purchase date (12/30/2022) and 2 years past the offering date (7/1/2022). Here’s what her tax treatment would be in this scenario:

Ordinary Income: $42.60 - $36.21= $6.39 / share x 392 = $2,505

Long Term Capital Gains: $55.60 -$42.60 = $13 / share x 392 shares = $5,096       

What is a Disqualifying Disposition?

If you fail to meet the either the 1 year from purchase OR 2 years from offering date holding period it is considered a disqualifying disposition. The worst tax decision is to sell shares less than a year from the purchase date(s), in which case you'll pay short term capital gains (which is the same as ordinary income) on the difference between the share price on the purchase date and your sale date. We won't address that scenario in our analysis.

What if Allison had elected to sell her stock after meeting the 1 year from purchase requirement but before the 2 year from offering date period? 

Ordinary Income: $47.94 - $36.21= $11.73 per share x 392 = $4,598

Long Term Capital Gain: $55.60 - $47.94 = $7.66 per share x 392 = $3,003

In Allison’s case, she’s in the 15% long term capital gains bracket and the 32% marginal income tax bracket so she would save $355 in federal tax through a qualified disposition.The total amount of tax from the ESPP sale is based on your personal household income tax bracket, which determines the capital gains brackets. This is why proper tax planning is essential to maximizing your ESPP investment.

Balancing ESPP Participation with Tax Planning

Because tax planning is critical to making the most of your ESPP, we advise with a financial advisor or tax professional to develop a strategy that aligns with your broader financial goals. At Ark Royal, we can help you create a balanced financial plan, optimizing your ESPP participation while minimizing tax implications.