7 Employee Stock Purchase Plan Questions to Answer

Before you Decide to Sign Up


At WestStar Prosperity Partners, we’ve helped our tech executive and professional clients (we call them ‘Aviators’) make the most of their equity compensation for years, giving them a clear view on how to optimize their stock positions and manage their tax obligations with confidence and clarity.

Equity based compensation is a great way to share in the potential profits of your company, but not fully understanding what you’ve been granted − or having a clear plan to make the most of it − can easily lead to costly mistakes, and a sense of lost opportunity. To manage the complexity that comes with your equity compensation takes time and effort.

Time stress is a common factor among ‘Aviators’ and so we help you understand and carefully manage the key concepts along with the terms and conditions of your grant.

Our ‘advice in plain English’ approach also covers the tax implications surrounding your compensation programs and we help you make decisions with a long-term financial plan in mind.

Our extensive knowledge of employer programs, combined with continuous monitoring of your financial plans helps to build an enduring relationship based on foundations of confidence, trust and teamwork.

That said, let’s take a look at the 7 questions to answer before you decide to sign up for your employee stock purchase plan.

  1. What is an ESPP?
  2. How does an ESPP work?

-How does ESPP enrollment work?

-What is the offering period?

-What is the purchase date?

-What is the purchase price?

  1. How can an ESPP help me with my financial plan?
  2. Will I end up owning too much company stock through an ESPP?
  3. Is an ESPP a good use of my money?
  4. How long is my money tied up in the stock?
  5. How are profits or losses from ESPPs reported for income tax purposes?

What Is An ESPP?

An employee stock purchase plan, or ESPP, offers an employee of a company the chance to sign up and then purchase shares of their employer’s stock systematically at a discount from market value.

You decide the amount you want to contribute and this is withheld (after-tax) from your paycheck and collected during the offering period, which is normally 3 to 6 months.

At the end of the offering period, the Plan Administrator buys shares with your funds and deposits them to your account.  You can either hold them or sell them for a potential immediate profit!

Many employees participate in an ESPP because they like the fact that they get to buy the company’s stock at a discount.  In some companies, this discount could be as high as 15%.

How Does An ESPP Work?

The way an ESPP works is fairly simple, comparative to other employee incentive programs. You fund the purchase of shares over time through payroll deductions. Typically, every pay period the amount you invest is withheld from your paycheck and collected during the offering period – normally 3 or 6 months. At the end of that period, the Plan Administrator uses your contributions to buy whole shares of Company stock (however much you can purchase at the discount), and the remainder of the money is rolled over into the next period.

How Does ESPP Enrollment Work?

Enrollment is usually done through a company’s online HR system, but could also be through a brokerage service. You just log on and indicate that you want to sign up for the plan. On the application, you will state the amount you want to contribute each pay period – usually limited to 10% of your take-home pay – and it often takes effect immediately.

What Is The Offering Period? 

For most companies, the offering period is every quarter or every six months. If you decided you wanted to enroll in the ESPP, you would be enrolled at the start of the next offering period.

What Is The Purchase Date?

The purchase date comes at the end of the offering period, and is the date that the money that’s been withheld gets invested in the actual stock. It is usually within a week after the quarter ends.

What Is The Purchase Price?

Companies have different formulas for deciding on the purchase price. Some like to look at the discount off the average price the stock traded at during the offering period. Some may view the price at the beginning of the offering period, and others, the end.

Some companies utilize lookback pricing – where they’ll look back and see where the actual low point was for the stock price over the offering period and make purchases based on that ‘lowest price’ during the period. This can be super beneficial to employees: you get as big of a discount as possible.

There’s some variability, but you can always find the specifics in the Company’s ESPP Summary Plan Description.

How Can An ESPP Help Me With My Financial Plan?

ESPPs can be a useful way for you to contribute money directly from your paycheck into your employer-offered plan, and to accumulate wealth.

One of the main benefits is that even if you don’t like the company’s stock itself, you’re getting a quick rate of return on your money by buying the stock and then selling it every 3 months or 6 months – as soon as you’re able to.

And even at an after-tax rate of return, it could be as high as 7-9%, which is fantastic.

It’s also an opportunity to systematically save through payroll, which has the benefit of being automatic. You sign up for the plan, and the rest just happens. It’s similar to a 401(k) in that regard, and that “set it and forget it” quality is part of what makes those plans be so successful in helping people build wealth.

An ESPP is not only a great program to generate an attractive rate of return, but from there, to be able to sell it immediately and utilize the money for expenses, to diversify your portfolio, or to buy another asset.  Alternatively, some people elect to hold on to the Company stock for the longer term.

It’s important to have an understanding of your cash flow, because an ESPP can be a very powerful tool. If you can get by without the money that’s going towards your ESPP contributions, it means you can make that money work for you.

Will I End Up Owning Too Much Company Stock Through An ESPP?

How much company stock to own is a very individual consideration. Employee Stock

Purchase Plans are often only part of a company’s total compensation package ─ a salary is part of it, a bonus could be part of it, and being given restricted stock units (RSUs) and/or other stock options might be another part of it.

Participating in an ESPP when you already have a lot of company stock through these other options could put you in a concentrated stock position, where a large portion of your money is tied to one stock ─ and at risk, if that company performs negatively versus the rest of the market.

Some of the questions we ask as we are working through the planning process include:

  • What percentage of your overall wealth or portfolio is concentrated in this one company’s stock?
  • How large and established is the company?
  • Is the company on a trajectory to continue growing and expanding?
  • How much is it growing, and what does the future look like for the sector?
  • In a worst-case type situation, how would your overall financial plan be affected in the case that your company stock declines by 30% or so?

It’s important to consider how comfortable you are with your company stock, which might depend on your own goals, your risk tolerance, how much you have in liquid savings, and what the potential is for your company.

Is An ESPP A Good Use Of My Money?

There’s no short answer here because it comes down to understanding each client and their individual needs. Our overall financial planning process will help us determine whether an ESPP is a good fit or not.

Part of planning is looking at your circumstances and asking the right foundational questions. How much do you have in checking and savings just for short-term needs? How much are you putting into retirement – what other plans does your employer offer, and are you maximizing those? What other monetary needs do you have? Are you comfortable being invested for some time, or do you have short-term financial goals that require liquid funds?

For a lot of people it makes perfect sense to participate in their ESPP, but as to the dollar amount which you should be contributing – that depends on your situation.

There is a maximum dollar amount that you can put into an ESPP, but that doesn’t necessarily mean that you should be meeting it. If you’ve got plenty of excess cash and a healthy cash flow, then maybe it makes sense; but if you’ve got other shorter-term goals, maybe it doesn’t at this moment in time. Something else to consider is that participating in an ESPP will reduce your take-home income because part of your paycheck will be going toward buying the company stock.

Coming up with a plan of how much to do and when to do it is something that requires an overall view of each individual’s unique situation and is something to work on with a financial planner.

The value of astute financial planning is simply immense, and that’s because it expresses your vision and builds your wealth towards achieving it. To find out what WestStar offers you within our comprehensive Aviator Financial Planning Suite, click here.

How Long Is My Money Tied Up In The Stock?

Most companies offer a buy-in over every quarter or six months, which means that every pay period over the quarter or six month offering period, your contributions are pulled directly from payroll and accumulate in your account until the purchase date.

At the end of the offering period (on the purchase date), your money is used to buy shares that are transferred to your account, and you can sell these immediately if you choose.

With many ESPPs, employees can withdraw from the plan at any time before the purchase date. However, you should refer to your plan documents to determine your plan’s rules governing withdrawals.

How Are Profits Or Losses From ESPPs Reported For Income Tax Purposes?

The specifics of this can be tricky and can change on a case-by-case basis. If you decide to sell the stock on the day that it vests, you’re going to pay ordinary income tax on the difference between what you sell the stock at and what it was purchased at.

That’s not a bad thing, because since you’re buying it at a discount, you’re locking in the gain.  If you decide to hold the stock, you may be able to get a more favorable tax treatment if you meet certain holding qualifications. There could be reasons to take either path – your financial situation and plan become the determining factors.

Why Hitch Your Wagon to WestStar?  

WestStar Prosperity Partners’ Advisor Team guides and mentors many highflyers. Our ‘advice in plain English’ approach brings confidence and clarity to managing your compensation programs, and we help you make and implement decisions with a long-term financial plan in mind.

Our advisors will help you turn the complex challenges into a clear flightpath to follow.

If you have questions about your specific circumstances, or want to talk further about how to make the most of your ESPP, please get in touch. We welcome the opportunity to chat with you.

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We wish you every success in the future and hope to hear from you soon.

Sam Gullette & Erik Alexander

Sam Gullette, CFP®, CLU®
Certified Financial Planner™

‘My mission in life is to help people take control of their money and avoid financial stresses. My clients are successful professionals and executives, many of whom are compensated heavily with company stock. Together we maximize their wealth-building opportunities, minimize taxes, and make sure their family is protected if life throws them a curveball.’

Erik Alexander
Financial Consultant

‘I work with professionals and executives who are compensated through various forms of company stock.  They have more money than time and struggle to balance the key aspects of their lives. Their decisions affect others, and they feel a huge responsibility towards making them wisely. I enjoy helping them solve their complex problems, and being counted on for their and their families’ financial wellbeing.’