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Sysco Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for Sysco Sysco partners with Aetna to provide its healthcare benefits to employees. Those enrolled in Sysco's national medical plan have access to various services through Aetna, including options for MinuteClinic appointments. Potential Healthcare Cost Increases in 2026 As we look ahead to 2026, Sysco employees can expect substantial increases in healthcare costs, reflecting broader trends in the industry. Nationwide, health insurance premiums for Affordable Care Act (ACA) plans are set to rise significantly, with some states forecasting hikes of over 60%. This surge is driven by a combination of expiring federal premium subsidies and ongoing medical cost inflation, leaving many enrollees at risk of facing out-of-pocket premium increases exceeding 75%. Consequently, it's imperative for individuals to prepare strategically to mitigate financial impact as these shifts unfold. Click here to learn more

'Sysco 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.

'Sysco 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.' Sysco 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. Sysco 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 Sysco 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 Sysco 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 Sysco 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 Sysco 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 Sysco 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 Sysco 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 type of retirement plan does Sysco offer to its employees?

Sysco offers a 401(k) Savings Plan to help employees save for retirement.

Does Sysco provide a matching contribution for its 401(k) plan?

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

At what age can Sysco employees start participating in the 401(k) Savings Plan?

Sysco employees can typically start participating in the 401(k) Savings Plan as soon as they meet the eligibility requirements, usually at age 21.

How can Sysco employees enroll in the 401(k) Savings Plan?

Sysco employees can enroll in the 401(k) Savings Plan through the company’s benefits portal or by contacting the HR department for assistance.

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

Sysco's 401(k) Savings Plan offers a variety of investment options, including mutual funds, target-date funds, and company stock.

How much can Sysco employees contribute to their 401(k) plan each year?

Sysco employees can contribute up to the IRS limit for 401(k) contributions, which is adjusted annually.

Does Sysco allow employees to take loans from their 401(k) Savings Plan?

Yes, Sysco allows employees to take loans from their 401(k) Savings Plan under certain conditions.

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

If a Sysco employee leaves the company, they can choose to roll over their 401(k) account to another retirement plan, cash out, or leave it with Sysco.

Can Sysco employees change their contribution percentage to the 401(k) plan?

Yes, Sysco employees can change their contribution percentage to the 401(k) plan at any time, subject to certain guidelines.

Is there a vesting schedule for Sysco's matching contributions to the 401(k) plan?

Yes, Sysco has a vesting schedule for its matching contributions, meaning employees must work for a certain period before they fully own those contributions.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Sysco offers a defined benefit pension plan that was frozen on December 31, 2012. Employees hired before this date continue to accrue vesting service. Benefits are calculated based on 1.5% of eligible career earnings through the freeze date. Additionally, Sysco provides a generous 401(k) plan with automatic and matching contributions. The company automatically contributes 3% of eligible pay to employees' 401(k) accounts, and matches 50 cents for every dollar contributed up to 6% of pay. Employees are automatically enrolled at a 3% contribution rate, with annual increases until reaching 6%.
Layoffs and Restructuring: In 2024, Sysco implemented layoffs across various departments without publicly detailing the reasons. This follows similar restructuring efforts in previous years aimed at improving financial performance amidst economic challenges and rising supply chain costs (Sources: Peek Career, Layoff Insider). Union Strike: In early 2023, union workers at Sysco's Indianapolis distribution hub went on strike, demanding better wages, benefits, and shorter working hours. This labor unrest highlights ongoing challenges in employee relations and operational disruptions (Source: WBOI). Financial Performance: Despite the layoffs, Sysco reported strong financial health in 2024, with initiatives to enhance core business operations, invest in infrastructure like new distribution centers, and expand its electric vehicle fleet (Source: Sysco).
Sysco includes RSUs in its compensation packages, vesting over a specific period and converting into shares. Stock options are also provided, enabling employees to purchase shares at a predetermined price.
Sysco has made several significant updates to its healthcare benefits over the past few years, reflecting the company's commitment to supporting employee well-being amidst rising healthcare costs. For 2023, Sysco maintained stable premiums for medical, dental, and vision plans for non-union employees despite the general trend of increasing healthcare costs. Additionally, Sysco expanded its benefits to include domestic partner coverage across all Health & Welfare plans, such as medical, dental, vision, life insurance, and critical illness coverage. These changes highlight Sysco's efforts to adapt to the evolving needs of its workforce and ensure comprehensive coverage for employees and their families. In 2024, Sysco introduced several enhancements, including increased contribution limits for Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs). The HSA limit for individual coverage rose to $4,150, while family coverage increased to $8,300, with catch-up contributions allowed for those 55 and older. The FSA limit also saw an increase, allowing employees to save up to $3,200. Sysco continues to offer various wellness programs, such as Headspace for mental health and Bloom for pelvic health, reflecting a holistic approach to employee well-being. These updates are particularly crucial in the current economic, investment, tax, and political environment, where healthcare costs and access are major concerns for employees.
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For more information you can reach the plan administrator for Sysco at 1390 enclave pkwy Houston, TX 77077; or by calling them at 1-281-584-1390.

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

*Please see disclaimer for more information

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