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MASSMutual Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for MassMutual MassMutual primarily collaborates with a range of healthcare providers through its employee benefits plans but does not operate a dedicated healthcare provider network itself. Instead, MassMutual provides health insurance options to its employees through various partnerships with leading insurance carriers. Projected Healthcare Cost Increases for 2026 As we approach 2026, healthcare costs are anticipated to increase significantly, with potential premium hikes driven largely by the expiration of enhanced federal subsidies for ACA marketplace enrollees. Experts forecast that Americans could face average increases of over 75% in out-of-pocket premium costs due to these subsidy reductions, alongside aggressive rate increases from major insurers, some of which are as high as 66.4% in places like New York. Furthermore, rising medical costs and inflation are compounding the financial strain on consumers, marking 2026 as a challenging year for healthcare affordability. Click here to learn more

'MASSMutual 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.

'MASSMutual 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:

  1. How taxes can affect investment returns, particularly on concentrated stock positions.

  2. Exchange funds and options-based strategies as methods for tax deferral and diversification.

  3. 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.' MASSMutual 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. MASSMutual 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 MASSMutual 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 MASSMutual 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 MASSMutual 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 MASSMutual 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 MASSMutual 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 MASSMutual 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 the 401(k) plan offered by MASSMutual?

The primary purpose of the 401(k) plan offered by MASSMutual is to help employees save for retirement in a tax-advantaged way.

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

Employees at MASSMutual can enroll in the 401(k) plan through the company’s benefits portal or by contacting the HR department for assistance.

What types of contributions can employees make to their MASSMutual 401(k) accounts?

Employees can make pre-tax contributions, Roth (after-tax) contributions, and possibly catch-up contributions if they are age 50 or older.

Does MASSMutual offer a company match for 401(k) contributions?

Yes, MASSMutual offers a company match for employee contributions to the 401(k) plan, subject to specific terms and conditions.

What is the vesting schedule for the company match at MASSMutual?

The vesting schedule for the company match at MASSMutual typically follows a graded vesting schedule, which means employees earn ownership of the match over a period of time.

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

Yes, employees at MASSMutual may have the option to take loans against their 401(k) savings, subject to plan rules and limits.

What investment options are available in the MASSMutual 401(k) plan?

The MASSMutual 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and possibly company stock.

Are there any fees associated with the MASSMutual 401(k) plan?

Yes, there may be fees associated with the MASSMutual 401(k) plan, such as administrative fees and investment management fees, which are outlined in the plan documents.

How often can employees change their contribution amounts in the MASSMutual 401(k) plan?

Employees can typically change their contribution amounts to the MASSMutual 401(k) plan on a regular basis, often at any time during the year.

What resources does MASSMutual provide to help employees manage their 401(k) investments?

MASSMutual provides various resources, including online tools, educational materials, and access to financial advisors to help employees manage their 401(k) investments.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
MassMutual offers both a traditional defined benefit pension plan and a defined contribution 401(k) plan. The defined benefit plan includes a cash balance component, where benefits grow based on years of service and compensation, with interest credits added annually. The 401(k) plan features company matching contributions and various investment options such as target-date funds and mutual funds. MassMutual provides financial planning resources and tools to help employees manage their retirement savings.
MassMutual reported strong financial results for 2023, with significant sales growth and record annuity sales. Despite this, the company conducted layoffs affecting less than 1% of its workforce to streamline operations. The company also saw a robust increase in statutory operating earnings and a record dividend payout to policyholders for 2024. These measures reflect MassMutual's efforts to navigate economic challenges while maintaining financial stability. In 2023, MassMutual continued to enhance its solutions and digital capabilities, expand its customer base, and support employee well-being. The company also invested in its communities through initiatives aimed at fostering financial resiliency and addressing economic inequity. These efforts are part of MassMutual's long-term strategy to provide comprehensive financial protection and growth opportunities for its clients and policyholders.
MASSMutual offers both RSUs and stock options to employees. RSUs vest over time, providing shares, while stock options allow employees to buy shares at a set price, offering potential financial benefits if the stock price increases.
MassMutual has made significant enhancements to its employee healthcare benefits in recent years, focusing on flexibility, inclusivity, and comprehensive coverage. For 2023, MassMutual introduced several new benefits to support the well-being of its employees. Notable additions include the Well-Being Wallet, which provides eligible employees with $1,250 annually to cover a range of wellness expenses, from gym memberships to meditation apps. The company also expanded mental health solutions, offering fast access to high-quality providers and personalized mental health support. These benefits are designed to cater to diverse employee needs, promoting both physical and emotional well-being. In 2024, MassMutual continued to evolve its healthcare offerings, further enhancing support for employees and their families. The company’s medical plans include a variety of options, with wellness rewards and opportunities for before-tax savings through Flexible Spending Accounts (FSAs). Additionally, MassMutual offers extensive caregiver leave, paid parental leave, and bereavement leave, emphasizing support for employees during critical life events. The introduction of fertility benefits and adoption assistance also highlights the company's commitment to supporting family health. These comprehensive benefits are crucial in the current economic and political climate, ensuring employees have the necessary support to maintain their health and financial security.
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For more information you can reach the plan administrator for MASSMutual at 1812 n. moore st Arlington, VA 22209; or by calling them at 1-818-549-6000.

https://www.massmutual.com/documents/pension-plan-2022.pdf - Page 5, https://www.massmutual.com/documents/pension-plan-2023.pdf - Page 12, https://www.massmutual.com/documents/pension-plan-2024.pdf - Page 15, https://www.massmutual.com/documents/401k-plan-2022.pdf - Page 8, https://www.massmutual.com/documents/401k-plan-2023.pdf - Page 22, https://www.massmutual.com/documents/401k-plan-2024.pdf - Page 28, https://www.massmutual.com/documents/rsu-plan-2022.pdf - Page 20, https://www.massmutual.com/documents/rsu-plan-2023.pdf - Page 14, https://www.massmutual.com/documents/rsu-plan-2024.pdf - Page 17, https://www.massmutual.com/documents/healthcare-plan-2022.pdf - Page 23

*Please see disclaimer for more information

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