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Cboe Global Markets Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Cboe Global Markets Cboe Global Markets provides health insurance through a comprehensive benefits package that typically includes coverage via larger national insurers, including UnitedHealthcare and Anthem Blue Cross Blue Shield, among others. These providers offer a range of healthcare plans and services that cater to the diverse needs of Cboe employees. Potential Healthcare Cost Increases in 2026 As the health insurance landscape evolves, Cboe Global Markets employees should prepare for significant increases in their healthcare costs. In 2026, premiums for Affordable Care Act (ACA) plans are projected to surge, with certain states experiencing hikes of over 60%. Contributing factors include the potential expiration of enhanced federal subsidies, ongoing medical inflation, and escalating costs of specialty drugs. These changes could significantly impact employees' out-of-pocket expenses, necessitating careful financial planning and consideration of more economical healthcare options. Click here to learn more

'Cboe Global Markets 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.

'Cboe Global Markets 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.' Cboe Global Markets 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. Cboe Global Markets 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 Cboe Global Markets 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 Cboe Global Markets 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 Cboe Global Markets 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 Cboe Global Markets 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 Cboe Global Markets 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 Cboe Global Markets 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 savings plan does Cboe Global Markets offer to its employees?

Cboe Global Markets offers a 401(k) retirement savings plan to its employees.

Can employees of Cboe Global Markets contribute to their 401(k) plan?

Yes, employees of Cboe Global Markets can contribute a portion of their salary to their 401(k) plan.

What is the maximum contribution limit for the Cboe Global Markets 401(k) plan?

The maximum contribution limit for the Cboe Global Markets 401(k) plan is determined by IRS regulations and may change annually.

Does Cboe Global Markets offer a matching contribution for its 401(k) plan?

Yes, Cboe Global Markets provides a matching contribution to eligible employees' 401(k) accounts.

When can employees at Cboe Global Markets enroll in the 401(k) plan?

Employees at Cboe Global Markets can enroll in the 401(k) plan during their initial onboarding period or during the annual open enrollment period.

Are there vesting requirements for the matching contributions at Cboe Global Markets?

Yes, Cboe Global Markets has a vesting schedule for matching contributions, which means employees must work for the company for a certain period before they fully own those contributions.

What investment options are available in the Cboe Global Markets 401(k) plan?

The Cboe Global Markets 401(k) plan offers a variety of investment options, including mutual funds and target-date funds.

How can employees of Cboe Global Markets access their 401(k) account information?

Employees of Cboe Global Markets can access their 401(k) account information through the company's designated retirement plan portal.

Can employees take loans against their 401(k) balance at Cboe Global Markets?

Yes, Cboe Global Markets allows employees to take loans against their 401(k) balance, subject to specific terms and conditions.

What happens to the 401(k) plan if an employee leaves Cboe Global Markets?

If an employee leaves Cboe Global Markets, they can choose to roll over their 401(k) balance to another retirement account, cash out, or leave it in the Cboe Global Markets plan if eligible.

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

In 2024, Cboe Global Markets announced a restructuring plan that includes reducing its workforce by 10% as part of a broader cost-cutting initiative aimed at streamlining operations and focusing on core business areas. The company also revealed changes to its employee benefits package, including reductions in healthcare coverage and adjustments to retirement plan contributions.

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For more information you can reach the plan administrator for Cboe Global Markets at 400 S. LaSalle St. Chicago, IL 60605; or by calling them at +1 312-786-5600.