Amazon Employees: Smarter Ways to Manage Taxes on Appreciated Stock
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As we approach 2026, healthcare costs are projected to rise significantly, a trend attributed to various factors including the potential expiration of enhanced federal premium subsidies associated with the Affordable Care Act (ACA). Many states are bracing for steep premium hikes, with some individual markets seeing increases exceeding 60%, which could push out-of-pocket costs for consumers up by more than 75%. This perfect storm of escalating medical expenses, combined with insurers pursuing aggressive rate hikes, underscores the urgent need for consumers to prepare for the financial implications of rising healthcare costs in the coming year.
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'Amazon 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.
'Amazon 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.
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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.' Amazon 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. Amazon 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 Amazon 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.
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This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Amazon 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.
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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 Amazon 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 Amazon 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 Amazon 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 Amazon employees who hold highly-appreciated stock.
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.
What type of retirement savings plan does Amazon offer to its employees?
Amazon offers a 401(k) retirement savings plan to its employees.
Does Amazon match employee contributions to the 401(k) plan?
Yes, Amazon provides a matching contribution for employee contributions to the 401(k) plan, up to a certain percentage.
How can Amazon employees enroll in the 401(k) plan?
Amazon employees can enroll in the 401(k) plan through the employee benefits portal after meeting eligibility requirements.
What is the eligibility requirement for Amazon employees to participate in the 401(k) plan?
Typically, Amazon employees are eligible to participate in the 401(k) plan after completing a specified period of service.
What investment options are available in Amazon's 401(k) plan?
Amazon's 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and company stock.
Can Amazon employees change their contribution percentage to the 401(k) plan?
Yes, Amazon employees can change their contribution percentage at any time through the employee benefits portal.
What is the maximum contribution limit for Amazon employees participating in the 401(k) plan?
The maximum contribution limit for Amazon employees is set by the IRS and may change annually; employees should check the current limits.
Does Amazon allow employees to take loans against their 401(k) savings?
Yes, Amazon allows employees to take loans against their 401(k) savings, subject to certain terms and conditions.
What happens to an Amazon employee's 401(k) if they leave the company?
If an Amazon employee leaves the company, they can choose to roll over their 401(k) balance to another retirement account, leave it with Amazon, or cash it out.
Are there any fees associated with Amazon's 401(k) plan?
Yes, there may be fees associated with managing the investments within Amazon's 401(k) plan, which are disclosed in the plan documents.
With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
401(k) plan with company match, various investment options and financial planning resources.
Amazon announced its largest layoffs in company history, affecting over 27,000 employees in 2023-2024. This includes 18,000 roles cut in January 2023 and an additional 9,000 announced in March 2023. The layoffs impact various divisions, including Amazon Web Services (AWS), People Experience and Technology (PXT), advertising, and Twitch. These decisions are part of Amazon's efforts to streamline operations and cut costs amidst declining retail sales and economic uncertainty. Amazon CEO Andy Jassy emphasized the need to be leaner while continuing to invest in key long-term customer experiences. Employees affected by the layoffs are being provided with separation payments, transitional health insurance benefits, and external job placement support.
Amazon.com Inc. provides stock options (SOs) and Restricted Stock Units (RSUs) as part of its compensation. SOs allow employees to buy stock at a set price after vesting. RSUs vest over four years, with a specific schedule: 5% after the first year, 15% after the second, and 20% every six months for the remaining two years. In 2022, Amazon emphasized performance-based RSUs. In 2023, Amazon adjusted equity strategies to align with market conditions. By 2024, Amazon expanded RSU programs to include more employees. Executives, management, and broader employees are eligible for these plans. [Source: Justia, 2022 Employee Stock Plan; MyStockOptions; Consilio Wealth Advisors]
Amazon offers a comprehensive and competitive benefits package aimed at supporting the diverse needs of its employees. For 2023, Amazon provided a range of healthcare options, including medical, dental, and vision plans that begin on the first day of employment. These plans include Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs) to help employees manage out-of-pocket healthcare expenses. Amazon also expanded its mental health resources, offering free counseling sessions, 24/7 virtual mental health support through the Twill app, and specialized support for children's mental health through a partnership with Brightline. These enhancements underscore Amazon’s commitment to supporting the well-being of its workforce. In 2024, Amazon continues to build on its robust benefits offerings. The company has introduced additional wellness programs, including emergency savings funds and financial assistance programs, to help employees prepare for unexpected expenses. Moreover, Amazon has improved its paid parental leave policies, providing up to 20 weeks of paid leave for birth parents and six weeks for eligible supporting parents. This holistic approach to employee benefits is particularly important in today’s economic and political climate, where healthcare affordability and access are critical issues. By continually updating its benefits package, Amazon ensures its employees are well-supported in maintaining their health and financial security.
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