What Is an ESPP and How Can You Make the Most of It?

Do you have ESPP grants but aren't quite sure how to manage them?

account_circle
By altshare Team
calendar_today
July 24, 2025

An Employee Stock Purchase Plan (ESPP) is one of the most valuable benefits a company can offer, giving employees the chance to buy company shares at a discounted price. It can be a powerful tool to increase your investment in the company you work for, but it's important to know how to use it wisely to avoid unnecessary mistakes.

Here are some key points to help you get started:

1. Understand Your Plan - and Ask Questions

Each ESPP has its own terms, including eligibility, discounts, and holding periods. Make sure to review the details. If anything is unclear, reach out to your plan trustee, they can explain specific terms and help clarify the tax implications.

2. How Does Your ESPP Work?

Every month, a portion of your salary is set aside to purchase shares at the end of a defined period (typically 3–12 months).
Example:

  • Jan 1, 2025: share price = $100
  • Jul 1, 2025: share price = $200

You purchase at a 15%discount from the lower price = $85
That means you’ve effectively bought a $200 share for $85 - a strong return from day one.

3. Know the Marginal Tax Rate

If your ESPP is under Section 102 with a trustee, a maximum marginal tax of 62.17% may be withheld:

  • 47% income tax
  • 3% surtax
  • 12.17% social/health insurance

This is a withholding rate, meaning it's the amount deducted in advance but not necessarily your actual tax liability. If your personal tax rate is lower than the amount withheld, the difference will be refunded: if you’re still employed by the company, the refund will typically be included in your next paycheck; if you’re no longer employed, you’ll need to file a tax return (Form 106) the following year to report your actual liability and receive any refund you’re entitled to.

4. Form 867 - Withholding Certificate

After selling your shares, your trustee will usually issue Form 867 the following year. This document confirms tax withheld on capital gains (if applicable) and is required for tax reporting.

5. Plan Your Sale

Company stock can fluctuate. Holding too much may increase your risk. Selling strategically can help manage exposure and lock in profits.

6. Evaluate the Benefits

When structured well, ESPPs offer strong returns on relatively low-risk contributions. It's worth reviewing how your plan fits into your broader financial strategy.

A Closer Look: ESPP Under Israeli Section 102

There are two primary tax routes:

1. Section 102 With a Trustee

If your ESPP is set up under Section 102 with a trustee, the main advantage is potential tax relief, but the timing of your sale matters.

Sell the shares before holding them for two years under the trustee’s custody? All gains are taxed as employment income, including income tax, social security, and health tax.

Hold the shares for at least two years from the ESPP purchase date?

Then:

• The portion equal to the discount is taxed as employment income.

• Any additional gain is considered capital gain and taxed at 25% (plus surtax if applicable).

Example:

Bought at $100, market value $150, sold at $190 after 2 years:

• $50 taxed as income

• $40 taxed as capital gain

2. Section 102 Without a Trustee

In this plan, income tax is withheld at the end of the offering period, when the shares are transferred to you. The tax applies to the benefit, the difference between the market value at that time and the discounted purchase price you paid.

Any future sale, even one day later, is subject to capital gains tax, but only on the increase beyond that end-of-offering-period value.

Once the shares are transferred, any future sale, whether one day or one year later, results in capital gains tax on the increase above the share value at the end of the offering period.

 

To conclude, your ESPP can be a powerful way to build investments and benefit from your company's success, but only if you take the time to really understand it. Ask questions, plan your sales, and think of it as one piece of your bigger financial puzzle. It’s not just about getting a discount; it’s about making smarter choices with what you already earn.

If you have any questions on how to optimize your ESPP grants or navigate the tax rules, we are here to assist - contactus@altshare.com

About altshare

altshare is a leading, fast-growing Equity Management & Compensation Plans Administration solutions provider. We love challenges. We are obsessed with our clients. We are on a mission to redefine the way founders do equity. All our products & services are supported through the altshare Platform - the only equity management platform built for entrepreneurs.

Back To Blog