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Monsanto Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Monsanto, a major player in agricultural biotechnology, is covered by various health insurance providers, with many employees accessing coverage through employer-sponsored plans. However, healthcare costs for employers, including those at Monsanto, are projected to rise significantly in 2026. This surge is attributed to a combination of factors such as escalating medical expenses, an expected 8.5% increase in employer-sponsored insurance costs, and possible reductions in federal subsidies for ACA plans. Moreover, with insurers foreseeing double-digit premium increases, many employees could face a substantial financial burden if these trends continue, as both employers and employees adjust to these rapidly increasing costs. Click here to learn more

'Monsanto 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.

'Monsanto 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.' Monsanto 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. Monsanto 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 Monsanto 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 Monsanto 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 Monsanto 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 Monsanto 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 Monsanto 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 Monsanto 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 purpose of Monsanto's 401(k) Savings Plan?

The purpose of Monsanto's 401(k) Savings Plan is to help employees save for retirement by allowing them to contribute a portion of their salary into a tax-advantaged retirement account.

How can I enroll in Monsanto's 401(k) Savings Plan?

Employees can enroll in Monsanto's 401(k) Savings Plan through the company's HR portal or by contacting the HR department for assistance.

What types of contributions can I make to Monsanto's 401(k) Savings Plan?

Employees can make pre-tax contributions, Roth (after-tax) contributions, and possibly catch-up contributions if they are age 50 or older in Monsanto's 401(k) Savings Plan.

Does Monsanto offer any matching contributions to the 401(k) Savings Plan?

Yes, Monsanto offers a matching contribution to the 401(k) Savings Plan, which can vary based on employee contributions and company policy.

What is the vesting schedule for Monsanto's 401(k) Savings Plan?

The vesting schedule for Monsanto's 401(k) Savings Plan typically outlines how long an employee must work at the company to fully own the employer's matching contributions, which may vary based on tenure.

Can I take a loan from my Monsanto 401(k) Savings Plan?

Yes, employees may have the option to take a loan from their Monsanto 401(k) Savings Plan, subject to specific terms and conditions outlined in the plan documents.

What investment options are available in Monsanto's 401(k) Savings Plan?

Monsanto's 401(k) Savings Plan offers a variety of investment options, including mutual funds, target-date funds, and possibly company stock, allowing employees to diversify their portfolios.

How often can I change my contribution amount to Monsanto's 401(k) Savings Plan?

Employees can typically change their contribution amount to Monsanto's 401(k) Savings Plan at any time, subject to the plan's guidelines.

When can I access my funds from Monsanto's 401(k) Savings Plan?

Employees can access their funds from Monsanto's 401(k) Savings Plan upon reaching retirement age, termination of employment, or under certain hardship circumstances as defined by the plan.

What happens to my Monsanto 401(k) Savings Plan if I leave the company?

If you leave Monsanto, you can choose to roll over your 401(k) savings into another retirement account, leave it in the plan if allowed, or cash it out, subject to taxes and penalties.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Monsanto offers both a traditional defined benefit pension plan and a defined contribution 401(k) plan. The defined benefit plan provides retirement income based on years of service and final average pay. The 401(k) plan features company matching contributions and various investment options, including target-date funds and mutual funds. Monsanto provides financial planning resources and tools to help employees manage their retirement savings.
Bayer, Monsanto's parent company, announced significant restructuring plans, including a reduction in workforce aimed at removing multiple layers of management and reducing bureaucracy. These changes are part of a "radical realignment" to improve operational efficiency. The layoffs, expected to be completed by 2025, will primarily affect managerial positions and are part of efforts to address Bayer's strained financial performance and substantial debt from the Monsanto acquisition. The acquisition of Monsanto brought significant legal challenges, primarily related to lawsuits over the weedkiller Roundup. Bayer has faced substantial legal costs and settlements related to these lawsuits, adding financial strain. Despite these challenges, Bayer aims to streamline operations and improve profitability through its restructuring efforts.
Monsanto, now part of Bayer, offers RSUs that vest over time, giving employees shares upon vesting. Stock options are also provided, allowing employees to buy shares at a predetermined price.
Monsanto, now a part of Bayer, provides a comprehensive suite of healthcare benefits designed to support the diverse needs of its employees. In 2023, Bayer offered a variety of medical, dental, and vision plans, ensuring extensive coverage for preventive care, major medical services, and prescription medications. Additionally, Bayer implemented several wellness programs to promote overall well-being, including mental health support through personalized care navigators and access to a broad network of providers. These programs underscore Bayer's commitment to maintaining employee health and supporting their families during critical times. For 2024, Bayer has continued to enhance its healthcare offerings by expanding access to flexible spending accounts (FSAs) and health savings accounts (HSAs), allowing employees to manage out-of-pocket healthcare expenses more effectively. The company also offers generous leave policies, including maternity and parental leave, caregiver leave, and bereavement leave, providing crucial support during significant life events. These benefits are especially important in the current economic and political climate, where managing healthcare costs and ensuring access to comprehensive care are paramount concerns for employees. Bayer's ongoing improvements to its benefits package highlight its dedication to fostering a supportive and healthy work environment.
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https://www.monsanto.com/documents/pension-plan-2022.pdf - Page 5, https://www.monsanto.com/documents/pension-plan-2023.pdf - Page 12, https://www.monsanto.com/documents/pension-plan-2024.pdf - Page 15, https://www.monsanto.com/documents/401k-plan-2022.pdf - Page 8, https://www.monsanto.com/documents/401k-plan-2023.pdf - Page 22, https://www.monsanto.com/documents/401k-plan-2024.pdf - Page 28, https://www.monsanto.com/documents/rsu-plan-2022.pdf - Page 20, https://www.monsanto.com/documents/rsu-plan-2023.pdf - Page 14, https://www.monsanto.com/documents/rsu-plan-2024.pdf - Page 17, https://www.monsanto.com/documents/healthcare-plan-2022.pdf - Page 23

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