New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

Dollar Tree Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Dollar Tree Dollar Tree, a prominent discount retail chain, offers health insurance benefits to its employees through a partnership with a healthcare provider. This provider typically includes a variety of plan options, which often encompass major medical insurance, dental, and vision coverage, specifically designed to cater to the diverse needs of its workforce. Potential Healthcare Cost Increases in 2026 As Dollar Tree prepares for 2026, it faces the risk of significant healthcare cost increases primarily driven by unfavorable external factors. A recent analysis indicates that without the continuation of enhanced federal premium subsidies, many employees may confront premium hikes of over 75%, significantly impacting out-of-pocket expenses. Coupled with rising medical inflation, expected to remain between 7.5% and 8.5%, employees might struggle with increased healthcare costs while also experiencing pressure from higher wage demands and adjustments in pricing models across the retail sector. These challenges may compel Dollar Tree to reevaluate its healthcare offerings and strategies to support its workforce. Click here to learn more

'Dollar Tree 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.

'Dollar Tree 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 Dollar Tree 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 Dollar Tree 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 Dollar Tree 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 401(k) plan offered by Dollar Tree?

The 401(k) plan offered by Dollar Tree is a retirement savings plan that allows employees to save a portion of their paycheck before taxes are taken out.

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

Dollar Tree employees can enroll in the 401(k) plan by completing the enrollment process through the company’s benefits portal or by contacting the HR department for assistance.

Does Dollar Tree match contributions to the 401(k) plan?

Yes, Dollar Tree offers a matching contribution to the 401(k) plan, which helps employees grow their retirement savings.

What is the maximum contribution limit for Dollar Tree's 401(k) plan?

The maximum contribution limit for Dollar Tree's 401(k) plan is in accordance with IRS guidelines, which may change annually.

When can Dollar Tree employees start contributing to the 401(k) plan?

Dollar Tree employees can start contributing to the 401(k) plan after they have completed their eligibility period, which is typically outlined in the employee handbook.

Are there any fees associated with Dollar Tree's 401(k) plan?

Yes, there may be administrative fees associated with Dollar Tree's 401(k) plan, which are disclosed in the plan documents provided to employees.

Can Dollar Tree employees take loans against their 401(k) savings?

Yes, Dollar Tree employees may have the option to take loans against their 401(k) savings, subject to the terms and conditions of the plan.

What investment options are available in Dollar Tree's 401(k) plan?

Dollar Tree's 401(k) plan typically offers a variety of investment options, including mutual funds and target-date funds, allowing employees to choose based on their risk tolerance.

How often can Dollar Tree employees change their 401(k) contributions?

Dollar Tree employees can change their 401(k) contribution amounts at designated times throughout the year, as specified in the plan guidelines.

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

If a Dollar Tree employee leaves the company, they have several options for their 401(k), including rolling it over to another retirement account or cashing it out, subject to tax implications.

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

Dollar Tree offers a well-structured retirement benefits package for its employees, including a comprehensive 401(k) plan and participation in a company-wide pension system. Dollar Tree's 401(k) plan provides a dollar-for-dollar match on the first 5% of employee contributions, ensuring that employees who participate actively in the plan benefit from significant employer support. In addition to the 401(k), employees can partake in the Employee Stock Purchase Plan, allowing them to buy company stock through automatic payroll deductions. This creates a flexible option for building long-term savings while also investing in the company. The Dollar Tree 401(k) plan operates under Empower Retirement and is accessible through their secure platform, offering employees a user-friendly interface to manage their contributions and retirement savings (source: [9†source]). Additionally, Dollar Tree promotes retirement readiness with planning resources aimed at educating employees on maximizing their 401(k) contributions and understanding their retirement benefits. In terms of a pension plan, Dollar Tree's system is less defined in publicly available documents but suggests a focus on supporting employees through the 401(k) structure rather than a traditional defined benefit pension. Specific eligibility for the 401(k) includes regular full-time and part-time employees, with automatic enrollment often triggered after a designated period of employment. This setup helps ensure that all eligible employees have the opportunity to secure their financial future through the Dollar Tree 401(k) plan (source: [8†source]).

Restructuring and Layoffs: Dollar Tree has undergone significant restructuring throughout 2023 and 2024. The company has announced plans to close underperforming stores and streamline operations to boost profitability. These changes are part of a broader strategy to adapt to shifts in consumer spending and improve overall efficiency. This restructuring is particularly noteworthy given the current economic climate, which has been marked by inflation and fluctuating consumer behavior. Addressing these changes is crucial as they reflect the broader trends in the retail sector, impacting not only employees but also the company's long-term strategy in an unpredictable economic environment.

Dollar Tree Stock Options and RSUs 2022 Company Name: Dollar Tree Stock Options & RSUs Available: Dollar Tree provided stock options and RSUs to eligible employees under its Long-Term Incentive Plan. Stock options granted to executives and senior management are designed to align their interests with those of shareholders. Source & Page Number: Annual Report 2022, page 49. Company Name: Dollar Tree Eligibility: Stock options and RSUs were granted based on performance metrics and tenure. Key executives and high-performing employees were prioritized. Source & Page Number: Proxy Statement 2022, page 18. 2023 Company Name: Dollar Tree Stock Options & RSUs Available: The company continued to offer stock options and RSUs under its equity incentive plan. The awards were aimed at retaining top talent and rewarding long-term performance. Source & Page Number: Annual Report 2023, page 53. Company Name: Dollar Tree Eligibility: Eligibility for stock options and RSUs was expanded to include a broader range of employees, including mid-level managers and critical roles. 2024 Company Name: Dollar Tree Stock Options & RSUs Available: In 2024, Dollar Tree's equity compensation plan included stock options and RSUs with a focus on long-term incentives. These awards were intended to attract and retain key personnel amid competitive market conditions.

Dollar Tree Official Website Healthcare Benefits Page: Dollar Tree provides information on health insurance, including medical, dental, and vision coverage, as well as wellness programs. Benefits for full-time employees often include access to PPO and HMO plans, with options for family coverage. Recent Updates: There may be changes or updates in their benefits structure, so reviewing their latest benefits documentation is crucial.

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For more information you can reach the plan administrator for Dollar Tree at 500 Volvo Pkwy Chesapeake, VA 23320; or by calling them at (757) 321-5000.