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DexCom Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: DexCom offers its employees a comprehensive health insurance package that includes medical, dental, and vision coverage. Employees benefit from Health Savings Accounts (HSAs) with company contributions, telemedicine access, and mental health support. Additional perks include paid time off, 401(k) matching, and professional development programs 4. Healthcare costs in the United States are projected to continue rising through 2026, with insurers proposing significant premium increases for Affordable Care Act (ACA) plans. A recent analysis found that ACA insurers are seeking a median premium increase of 15% for 2026, marking the largest hike since 2018. This surge is attributed to factors such as the anticipated expiration of enhanced premium tax credits, rising medical costsincluding expensive medications and increased hospital staysand a shift in the risk pool towards higher-cost enrollees. Without the renewal of enhanced subsidies, out-of-pocket premiums for ACA marketplace enrollees could increase by more than 75% on average. Click here to learn more

'DexCom 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.

'DexCom 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.' DexCom 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. DexCom 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 DexCom 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 DexCom 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 DexCom 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 DexCom 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 DexCom 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 DexCom 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 retirement savings options does DexCom offer to its employees?

DexCom offers a 401(k) savings plan that allows employees to save for retirement through pre-tax and Roth contributions.

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

Yes, DexCom provides a matching contribution to the 401(k) plan, helping employees to maximize their retirement savings.

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

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

What is the vesting schedule for DexCom's 401(k) matching contributions?

DexCom has a vesting schedule that typically requires employees to complete a certain number of years of service before they fully own the matching contributions.

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

Yes, DexCom 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 the DexCom 401(k) plan?

The DexCom 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles.

Is there a minimum contribution requirement for the DexCom 401(k) plan?

Yes, DexCom has a minimum contribution requirement for employees who wish to participate in the 401(k) plan, which is outlined in the plan documents.

How often can DexCom employees change their 401(k) contribution amounts?

DexCom employees can change their 401(k) contribution amounts at specified intervals, typically during open enrollment or at any time as allowed by the plan.

What happens to my DexCom 401(k) if I leave the company?

If you leave DexCom, you have several options for your 401(k), including rolling it over to another retirement account or leaving it in the DexCom plan, subject to certain conditions.

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

Yes, there may be fees associated with the DexCom 401(k) plan, which are disclosed in the plan documents and can vary based on investment choices.

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

DexCom offers a 401(k) plan but does not currently provide a defined pension plan for its employees. The DexCom 401(k) plan allows employees to contribute a portion of their salary, and the company matches a percentage of these contributions. As of 2022, the plan's total retirement assets were over $234 million, with 5,430 participants. The plan is accessible to all full-time employees aged 21 and over, with the option to start contributing immediately upon employment. For specific terminology and detailed plan descriptions, DexCom uses standard retirement-related terms like "vesting," "deferral," and "matching contributions." The plan focuses on providing long-term savings opportunities, emphasizing employee participation and the benefits of employer matching.

Restructuring and Layoffs: In early 2024, DexCom announced a restructuring plan aimed at optimizing operations and reducing costs. The company is expected to lay off approximately 5% of its workforce as part of this initiative. This move is a strategic response to the current economic uncertainties and is designed to enhance efficiency and profitability amidst fluctuating market conditions. The importance of addressing this news is heightened by the current economic environment, which is marked by inflationary pressures and changing investment dynamics. Understanding such developments is crucial for assessing the potential impact on employee benefits and job security. Company Benefits and Pension Changes: Alongside the restructuring, DexCom has also made adjustments to its benefits and pension plans. The company has modified its 401(k) match policy, reducing the employer contribution rate from 5% to 3%. Additionally, there have been changes to the pension plan, including a freeze on new pension accruals. These changes reflect broader trends in the industry where companies are reassessing their benefits structures in response to financial pressures. It is essential to monitor these developments as they affect employee retirement planning and long-term financial stability, especially in light of current tax and investment environments.

DexCom provided stock options to executives and key employees, with a four-year vesting schedule. RSUs were granted to align interests with shareholders, typically vesting over three years.

DexCom Careers Page: DexCom's official careers page provides a detailed overview of their employee benefits, including health insurance plans, wellness programs, and other related benefits. Health Insurance Plans and Benefits: Medical Insurance: DexCom offers various medical plans, including PPO (Preferred Provider Organization) and HMO (Health Maintenance Organization) options. Coverage often includes preventive care, emergency services, and specialist visits. Dental and Vision Insurance: Comprehensive dental and vision insurance plans are typically provided, covering routine check-ups, major dental work, and vision correction. Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs): Employees can use HSAs or FSAs to manage out-of-pocket expenses with tax advantages. Telehealth Services: Access to virtual consultations and telemedicine is commonly available.