ESPP How-To #3: Calendar Your Bets & Play to Win

Imagine a casino game that allowed you to bet once to get in the game and then withdraw your bet after you had more information and saw that you no longer wanted to take the bet.

To maximize your ESPP benefits, know your rights to make changes and withdrawals under your ESPP and calendar the key decision dates for those changes and withdrawals.

Changing Your Bets

The right to wait to make a final decision is always an advantage in a game, as the risk of loss or chances of winning change over time. In legal contracts, people often pay more for the right to make changes at a later time.

Your ESPP game may allow you to change your bets after the Offering Period has begun without charging you for the right to make this change. This gives you the opportunity to strategize for your purchases based on changes in the company’s stock price.

For example, if you’re following the stock price and find that the likely discount on the next Purchase Date will not be not high enough to make you want to make the purchase, you would want to cancel your bet and get a refund if your plan would allow it. If you’re following the stock price and decide you want to bet more to take advantage of an attractive Look Back discount (because of a low Offering Date market price), you would want to increase your payroll deduction percentage.

Even if your plan allows these changes, it will have very strict deadlines for each change. Calendar your decision dates for each possible change, follow the company’s stock price throughout each Purchase Period, and reconsider your bets as each Purchase Date approaches.   

Cisco Bet Change Opportunities

This timeline shows the timing of bet choices during a sample Cisco Offering Period.

Transient

Bet #1: Open Enrollment

Open Enrollment is the first phase of betting, as employees sign up to have a percentage of their income (1% to 10%) deducted at each pay period during the Offering Period (Contributions). This locks in their right to (automatically) purchase stock on each Purchase Date with a maximum Purchase Price of 85% of the market price on the first day of the Offering Period.

The only entrance time for playing an Offering Period is Open Enrollment, which takes place in the months before the start of an Offering Period. If employees don’t enroll and later find that the Offering Date market price was low and the Look Back discount is attractive, they’re out of luck as it’s too late to join that Offering Period.

Bet #2: Withdrawal During Purchase Period

Cisco’s ESPP includes the right to withdraw from the Offering Period (subject, of course, to strict timing deadlines). Withdrawing employees have the choice to (1) have all the Contributions accumulated during the current Purchase Period refunded (“withdraw-with-refund”) or (2) have those Contributions used for purchase on the next Purchase Date but cease all further payroll deductions (“withdraw-with-purchase”). Of course, purchases made on prior Purchase Dates are already final, and those funds will not be refunded.

The right to withdraw-with-refund makes it possible to monitor the stock price, predict the Purchase Price for upcoming Purchase Dates and choose not to make the purchase if the Purchase Price is unappealing.

For example, if an employee is not impressed with only a 15% discount, he or she could monitor the stock price and withdraw-with-refund during a Purchase Period in which he or she expects the market price on the Purchase Date to be less than the market price on the Offering Date.

However, withdrawal during a Purchase Period permanently removes an employee from the remainder of the Offering Period.

Bet #3: Decrease Payroll Deduction Percentage

Cisco allows employees to decrease their payroll deduction percentages, subject to strict deadlines. They can choose to have the decrease effective during the current Purchase Period or starting in the next Purchase Period.

Bet #4: Increase Payroll Deduction Percentage

Cisco allows employees to increase their payroll deduction percentages, subject to strict deadlines. However, payroll deduction percentage increases will not become effective until the following Purchase Period.

For example, an employee who is enrolled in an Offering Period during which the market price is rising above the Offering Date market price might want to increase his or her Contributions for the remaining Purchase Periods within that Offering Period to take advantage of an attractive Look Back discount.

Bet #5: Change Payroll Deduction Percentage for Next Offering Period

If an employee is still enrolled in the Cisco ESPP at the end of the Offering Period, he or she is automatically enrolled in the next Offering Period, which starts immediately after Purchase Date #4. If the employee chooses not to participate in the next Offering Period, or wants to increase or decrease the payroll deduction percentage for the next Offering Period, those changes should be made during Purchase Period #4.

Calendar to Win

Even if your plan allows these Cisco-style bet changes, like Cisco it will have very strict deadlines for each change. To take advantage of this flexibility and maximize your benefits:

Calendar your decision deadlines for each bet – open enrollment, withdrawal, decrease payroll deduction %, or increase payroll deduction %; Follow the company’s stock price throughout each Purchase Period; Make changes in your bets by the deadlines; and Be glad you played to win.

More in the ESPP How-To Series:

Intro To ESPPs

Timeline the ESPP

Know the Discount

Calendar Your Bets & Play to Win

Tax Basics

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Stock Option Counsel

We serve as Stock Option Counsel to employees and executives who want to maximize their stock compensation, including stock options, RSUs and restricted stock. 

ESPP How-To #2: Know the Discount

The discount is the “win” of an ESPP because it allows you to buy stock for less than the market price. Most ESPPs use a discount percentage of 5-15% off of the market price.

Big Win = Look Back Discount

The best ESPPs “look back” in time to calculate an even better discount for employees.

On the date of each purchase, an ESPP with a Look Back will calculate the purchase price by applying the discount percentage to the lesser of (1) the market price on a date months or even years before the Purchase Date (for Cisco, the Offering Date) or (2) the market price on the Purchase Date.

A Look Back is valuable if the market price of the company’s stock is rising during an Offering Period, as purchase prices during that Offering Period would be calculated using the low market price of the first day of the Offering Period (Offering Date).  For example, if the market price goes up from $10 to $20 over a tw0-year Offering Period and a company uses a 15% discount percentage, the purchase price on the last day of the Offering Period would be $8.50. That would be a discount of $11.50 off of the market price on that day.

Cisco’s Purchase Price Calculation

Cisco’s ESPP has a 15% discount and a two-year Look Back. Therefore, joining a Cisco Offering Period locks in the right to buy stock with a maximum price of 85% of the market price on the first day of that Offering Period. Even if the market price of the stock rises dramatically over the two years of the Offering Period, the employee’s maximum purchase price on each Purchase Date in that Offering Period is 85% of market price on the first day of that Offering Period.

Cisco’s Purchase Price on any Purchase Date is the LOWEST OF:

1. 85% of the market value of the stock on the Offering Date OR

2. 85% of the market value of the stock on the Purchase Date.

Transient

Cisco Up Market Example: If the market price on the Offering Date is $15 and the market price on the Purchase Date is $25, the Purchase Price for that Purchase Date would be $12.75 – 85% of $15. That would be a discount of 49% off of the market price on the Purchase Date. If the employee sold the stock immediately after the Purchase Date, he or she would have a gain (winnings) of $12.25 per share.

Cisco Down Market Example: If the market price on the Offering Date is $15 and the price has dropped to $10 on the Purchase Date, the Purchase Price for that Purchase Date would be $8.50 – 85% of $10. That would be a discount of 15% off of the market price on the Purchase Date. If the employee sold the stock immediately after the Purchase Date, he or she would have a gain (winnings) of $1.50 per share.

Cisco Reset Feature

Since the goal of an Offering Period game is to lock in the lowest possible Purchase Price, the Cisco ESPP automatically cancels any Offering Period after any Purchase Date on which the market price is less than the market price on the Offering Date. New Offering Periods start every six months, so participants are automatically enrolled in a new Offering Period starting after that Purchase Date. This lets employees take advantage of the lower maximum Purchase Price of the new Offering Period as the market price on the new Offering Date will be less than the market price on the cancelled Offering Period’s Offering Date. 

 

More in the ESPP How-To Series:

Intro To ESPPs

Timeline the ESPP

Know the Discount

Calendar Your Bets & Play to Win

Tax Basics

***

Stock Option Counsel

We serve as Stock Option Counsel to employees and executives who want to maximize their stock compensation, including stock options, RSUs and restricted stock.

ESPP How-To #1: Timeline the ESPP

Playing and winning the ESPP game is not as simple as writing a check to the company and receiving discounted stock. To maximize ESPP benefits, the first step is to understand the timeline of important events in your ESPP game.

In most ESPPs, the timeline flows like this: (1) employee enrolls to participate in an Offering Period and agrees to have the company deduct a percentage of his or her income to hold for later purchase of the company’s stock; (2) payroll deductions continue throughout the Offering Period; (3) the company holds onto the employee’s payroll deduction funds until special Purchase Dates; and (4) on each Purchase Date, the employee’s accumulated funds are automatically used to purchase discounted company stock for the employee.

Cisco ESPP Timeline

Cisco starts two games (Offering Periods) per year. Each Offering Period lasts for two years and has four six-month rounds (Purchase Periods) within it.

Transient

If a Cisco employee signs up for an Offering Period during Open Enrollment, he or she authorizes the company to take a percentage of his or her income at every pay period during the Offering Period (Contributions).

Cisco holds the employee’s Contributions on his or her behalf to purchase stock at the end of each Purchase Period within the Offering Period. The dates on which the purchases are made are called Purchase Dates.

Transient

Contributions accumulate during each Purchase Period. On the last day of each Purchase Period (the Purchase Dates), the employee’s Contributions are used to purchase Cisco stock at a discount. The company creates a special brokerage account for each employee and deposits the stock into that account after each Purchase Date.

More in the ESPP How-To Series:

Intro To ESPPs

Know the Discount

Calendar Your Bets & Play to Win

Tax Basics

Mary Russell counsels individual employees and founders to negotiate, maximize and monetize their stock options and other startup stock. She is an attorney and the founder of Stock Option Counsel. You are welcome to contact Stock Option Counsel at info@stockoptioncounsel or (650) 326-3412.