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Chewy Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Chewy Chewy Inc. primarily collaborates with CarePlus, its dedicated healthcare arm, to provide various pet wellness and insurance plans to its customers. CarePlus aims to enhance the health and wellness of pets through comprehensive healthcare services and plans. Potential Healthcare Cost Increases in 2026 In 2026, Chewy employees may face significant increases in healthcare costs, primarily driven by anticipated record hikes in Affordable Care Act (ACA) premiums. With reports indicating some states could see premium jumps exceeding 60%, coupled with the potential expiration of enhanced federal premium subsidies, many employees could experience monthly costs rising by over 75%. As Chewy employees evaluate their healthcare options, understanding these dynamics will be crucial for their financial planning and healthcare budgeting in the face of rising costs. Click here to learn more

'Chewy 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.

'Chewy 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.' Chewy 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. Chewy 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 Chewy 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 Chewy 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 Chewy 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 Chewy 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 Chewy 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 Chewy 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 401(k) plan offered by Chewy?

Chewy offers a 401(k) plan that allows employees to save for retirement through pre-tax contributions, helping them build a secure financial future.

Does Chewy match employee contributions to the 401(k) plan?

Yes, Chewy provides a matching contribution to the 401(k) plan, which helps employees maximize their retirement savings.

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

Chewy employees can enroll in the 401(k) plan through the company’s HR portal or by contacting the HR department for assistance.

What is the eligibility requirement for Chewy's 401(k) plan?

Employees at Chewy are typically eligible to participate in the 401(k) plan after completing a certain period of service, as specified in the plan documents.

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

Yes, Chewy allows employees to take loans against their 401(k) savings, subject to specific terms and conditions outlined in the plan.

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

Chewy's 401(k) plan offers a variety of investment options, including mutual funds, stocks, and bonds, allowing employees to tailor their investment strategy.

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

Chewy employees can change their 401(k) contributions at designated times throughout the year, typically during open enrollment periods or after a qualifying event.

Is there a vesting schedule for Chewy's 401(k) matching contributions?

Yes, Chewy has a vesting schedule for matching contributions, meaning employees must work for a certain period before they fully own the matched funds.

What happens to Chewy employees' 401(k) accounts if they leave the company?

If Chewy employees leave the company, they can choose to roll over their 401(k) balance to another retirement account, cash out, or leave it in the Chewy plan if permitted.

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

Yes, Chewy's 401(k) plan may have administrative fees and investment-related expenses, which are disclosed in the plan documents.

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

Chewy is undergoing a significant restructuring, which includes laying off approximately 10% of its workforce. This decision aligns with the company's strategy to streamline operations and reduce costs. The restructuring also involves changes to employee benefits and pension plans.