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Gartner Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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'Gartner employees with concentrated stock positions may benefit from thoughtful tax planning that allows for tax deferral while balancing liquidity, compliance, and long-term compounding,' Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Gartner employees who hold highly-appreciated stock may want to consider tax-efficient strategies that help mitigate their liabilities while aligning with their overall retirement goals,' Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How taxes can affect investment returns, particularly on concentrated stock positions.
Exchange funds and options-based strategies as methods for tax deferral and diversification.
Alternative planning techniques outside ETFs, including charitable trusts and gifting strategies.

By Carlos Hernandez, Wealth Enhancement advisor

When it comes to driving portfolio returns, many investors aim to keep management fees low by investing in low-cost index funds and exchange-traded funds (ETFs). While fees matter, however, the real culprit for lower-than-anticipated performance is taxes. ¹

Wealth Enhancement advisor Carlos Hernandez explains: 'By losing less to taxes each year, investors have access to more capital that can continue to compound over time. This makes tax deferral an important part of an effective financial plan.' Gartner employees looking for long-term growth strategies could benefit by understanding how to better manage their investment tax burdens.

Trade Money

One area where taxes can take a toll is on the sale of company stock or other concentrated investment positions. Gartner professionals looking to diversify could face significant capital gains taxes on an outright sale. One way to diversify without triggering immediate capital gains is through exchange funds. By contributing their highy-appreciated stock to a pooled fund, investors can trade their concentrated holdings for shares in a diverse basket of securities. This method can be used by Gartner employees who want to diversify while postponing taxable events.

Although this method allows for tax deferral, it also requires investors to hold the exchange fund for a period of time, typically seven years. ² This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Gartner executives should carefully evaluate.

Funds Based on Options

Another way to mitigate taxes on the sale of highly-appreciated stock is by using options contracts. The idea is to hedge risk with put options while covering the cost of those puts by selling call options—a strategy called 'collaring'. From there, the strategy reverses, with investors selling put options and using the proceeds to buy call option on an equity or bond index. ³ If managed effectively, this helps to diversify a concentrated portfolio while still maintaining liquidity.

Given the complexity of this strategy, meticulous planning is necessary. It's generally recommended that investors work with an experienced financial advisor before pursuing this approach.

Things to Be Aware of

Although these strategies can be beneficial for Gartner employees who hold highly-appreciated stock, caution is recommended. There are costs associated with these approaches, and potential liquidity risks. Additionally, the IRS may eventually contest such arrangements because their tax status has not been thoroughly examined—something Gartner retirees should keep top of mind.

'Tax drag reduction strategies can be effective, but they must be assessed through the lens of risk, liquidity, cost, and compliance,' warns Carlos Hernandez. What is appealing in theory must hold up to inspection in the real world.

Alternative Strategies

Although they show promise, investors with highly-appreciated stock or those looking to postpone gains have other alternatives besides exchange funds or options. Other tactics could include:

- Prepaid variable forwards (subject to IRS regulations, contracts to sell at predetermined terms in the future).
- Charitable remainder trusts (CRTs), which allow investors to donate appreciated stock to a charitable trust and receive a stream of regular income in return.
- Donor-advised funds (DAFs), which provide investors with a tax deduction for the fair market value of the appreciated stock they donate.
- Other gifting techniques, such as direct donations to charity or family.
Each has its own set of guidelines, advantages, and disadvantages. To limit unnecessary taxes or violating the constructive sale regulations, careful planning is necessary for Gartner professionals managing complex portfolios.

The Bottom Line

Although the movement to mitigate the tax burden on investments is not new, the instruments are changing. Both exchange funds and options-based structures offer investors a way to manage tax liabilities, especially for Gartner employees who hold highly-appreciated stock.

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In the end, taxes are unavoidable. However, with the correct set of instruments, they can be controlled and postponed. 'The real value comes from aligning tax strategy with investment strategy,' summarizes Carlos Hernandez.

Sources:

1. BlackRock Advisor Center. ' Investing for After-Tax Returns ,' 2025.

2. Kiplinger. ' Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings ,' by Robert Waskiewicz. Sep. 11, 2025.

3. Financial Planning Association. ' Tax-Efficient Ways to Diversify Concentrated Stock Positions ,' by Peter Lazaroff. Oct. 2024.

What is the primary purpose of Gartner's 401(k) plan?

The primary purpose of Gartner's 401(k) plan is to help employees save for retirement by providing a tax-advantaged account to accumulate savings over time.

How can Gartner employees enroll in the 401(k) plan?

Gartner employees can enroll in the 401(k) plan by accessing the employee benefits portal and following the enrollment instructions provided.

Does Gartner offer a company match for contributions to the 401(k) plan?

Yes, Gartner offers a company match for employee contributions to the 401(k) plan, which helps employees boost their retirement savings.

What types of investment options are available in Gartner's 401(k) plan?

Gartner's 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles to suit different risk tolerances.

Can Gartner employees change their contribution percentages at any time?

Yes, Gartner employees can change their contribution percentages at any time through the employee benefits portal, subject to certain plan rules.

What is the vesting schedule for the company match in Gartner's 401(k) plan?

The vesting schedule for the company match in Gartner's 401(k) plan typically follows a graded vesting schedule, which means employees earn rights to the company match over a period of time.

Are there any fees associated with managing Gartner's 401(k) plan?

Yes, there may be fees associated with managing Gartner's 401(k) plan, which can include administrative fees and investment management fees. Employees can review the fee structure in the plan documents.

How often can Gartner employees review their 401(k) account statements?

Gartner employees can review their 401(k) account statements quarterly, and they also have access to their account information online at any time.

What happens to a Gartner employee's 401(k) account if they leave the company?

If a Gartner employee leaves the company, they can choose to roll over their 401(k) account to another retirement plan, leave it in the current plan, or cash it out, subject to taxes and penalties.

Is there a loan option available within Gartner's 401(k) plan?

Yes, Gartner's 401(k) plan may offer a loan option, allowing employees to borrow against their account balance under certain conditions.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Plan Name: Gartner does not appear to have a defined benefit pension plan. The company primarily offers a defined contribution plan, which is a 401(k) plan. Years of Service and Age Qualification: Not applicable as Gartner does not offer a traditional pension plan. Plan Name: Gartner 401(k) Plan. Eligibility: Gartner's 401(k) Plan is generally available to all eligible employees. Eligibility typically depends on factors such as length of service and employment status. Employees usually become eligible to participate in the plan after completing a specified period of employment, often 30 days. Contribution Limits: Employees can contribute up to the IRS annual limit. Gartner may offer a match or other contributions, which should be detailed in the plan documents. Company Match: Gartner provides a matching contribution, though the specific percentage or formula should be verified in the most recent plan documents.

Restructuring and Layoffs: In early 2024, Gartner announced a significant restructuring plan, which included layoffs affecting approximately 5% of its global workforce. This decision comes as the company aims to streamline its operations and adapt to evolving market demands. The restructuring is part of Gartner's broader strategy to focus on high-growth areas and improve operational efficiency. Given the current economic climate, where companies are reevaluating their workforce and operational strategies, it is crucial to stay informed about such changes to understand their potential impact on the job market and broader economic conditions. Company Benefits, Pensions, and 401k Changes: Gartner has also made adjustments to its employee benefits, including modifications to its pension and 401k plans. The company has shifted to a more flexible 401k match program, which now varies based on individual performance and company profitability. Additionally, changes to the pension plan have been made to better align with current financial realities and investment returns. These changes are particularly important to follow in the context of fluctuating investment markets and evolving tax regulations, as they can directly affect retirement planning and financial security for employees.

Gartner provides stock options as part of its employee compensation package. These options typically vest over a period of time, offering employees the opportunity to purchase shares at a set price. Stock options are generally available to senior executives and other key employees.

Health Insurance: Gartner offers comprehensive health insurance options including medical, dental, and vision coverage. Wellness Programs: Includes access to wellness resources, mental health support, and employee assistance programs. Acronyms and Terms: Common terms include HSA (Health Savings Account), FSA (Flexible Spending Account), and EAP (Employee Assistance Program).