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Gartner Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Gartner Healthcare Provider Gartner collaborates with various healthcare providers and organizations to deliver research and insights that guide healthcare strategies. While specific healthcare partners may change over time, Gartner is known for providing expert consultancy in the healthcare sector, helping organizations optimize their technology and IT spending. Potential Healthcare Cost Increases in 2026 As we approach 2026, healthcare costs are projected to surge significantly, particularly within the Affordable Care Act (ACA) marketplace. Reports suggest that some states may experience premium hikes exceeding 60%, driven by a confluence of rising medical expenses, the potential expiration of enhanced federal subsidies, and aggressive rate increases by major insurers. Without action from Congress to extend these subsidies, about 92% of marketplace enrollees could face staggering increases of up to 75% in their out-of-pocket premiums, making affordability a pressing issue for millions. As healthcare consumers prepare for these anticipated changes, understanding these dynamics is crucial for navigating the evolving landscape of healthcare costs. Click here to learn more

'Gartner employees can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'Gartner employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations Gartner employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some Gartner employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by Gartner employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

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Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

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).