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The Boeing Company Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for The Boeing Company The Boeing Company offers health benefits through its partnership with various healthcare providers, primarily utilizing the health plans facilitated by Blue Cross Blue Shield and other regional providers, depending on the employees' locations. Potential Healthcare Cost Increases in 2026 for The Boeing Company In 2026, healthcare costs for employees at The Boeing Company are expected to rise significantly, fueled by anticipated premium hikes in the Affordable Care Act (ACA) marketplace. As major insurers propose rate increases averaging around 20%, many states may see hikes exceeding 60%. This increase is compounded by the potential expiration of enhanced federal premium subsidies, which could result in out-of-pocket premiums spiking by over 75% for the majority of policyholders. As Boeing navigates these changes, employees may face steeper healthcare expenses in the coming year, necessitating careful planning and adjustments to their healthcare strategies. Click here to learn more

'The Boeing Company 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.

'The Boeing Company 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.' The Boeing Company 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. The Boeing Company 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 The Boeing Company 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 The Boeing Company 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 The Boeing Company 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 The Boeing Company 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 The Boeing Company 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 The Boeing Company 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.

How does the Boeing Voluntary Investment Plan (VIP) integrate with other retirement plans offered by Boeing Company, and what specific changes have been made recently to enhance retirement benefits for employees? Discuss the implications these changes might have on employees planning their retirement.

The Boeing Voluntary Investment Plan (VIP) integrates with other Boeing retirement plans, such as the Boeing Pension Value Plan and other defined benefit plans. Recently, changes like the addition of a Roth contribution option and a shift toward enhanced defined contributions have been made to improve benefits for certain employees, particularly those who previously participated in both defined benefit and defined contribution plans. These changes enhance retirement planning flexibility but may require employees to adjust their strategies depending on their long-term financial goals.

What are the key eligibility requirements for participation in the Boeing Voluntary Investment Plan, and how do these requirements align with industry standards for retirement plans within large corporations? Specifically, address how the eligibility criteria impact various groups of employees within Boeing Company.

Key eligibility requirements for the Boeing VIP include no minimum age or service requirements, though certain groups, such as union employees and non-resident aliens, may be excluded. These criteria align with industry standards, making the plan accessible to a broad range of employees. The inclusivity of eligibility supports employees at various career stages, though exclusions may affect unionized employees or contractors differently from their non-union counterparts​(Boeing_Voluntary_Invest…).

In what ways does the Boeing Voluntary Investment Plan support employees who wish to make catch-up contributions, particularly for those nearing retirement age? Examine the financial benefits and potential challenges associated with these contributions for Boeing employees.

Boeing VIP allows catch-up contributions for employees aged 50 and over, aligning with IRS guidelines for retirement savings. This option benefits employees nearing retirement by enabling them to contribute more toward their savings. However, the increased financial burden of larger contributions could pose a challenge for employees with tighter budgets, potentially limiting their ability to maximize catch-up contributions​(Boeing_Voluntary_Invest…).

How does the investment allocation strategy within the Boeing Voluntary Investment Plan reflect the principles of risk management and diversification? Evaluate the types of investment options available and their relevance for Boeing employees planning for retirement.

The investment strategy of Boeing VIP emphasizes risk management and diversification, offering a wide range of options, including lifecycle funds, index funds, and company stock. These choices provide flexibility for employees with varying risk tolerances, helping them manage retirement savings effectively. The availability of different fund types ensures that employees can align their investment choices with their retirement timelines and risk preferences​(Boeing_Voluntary_Invest…).

What options does the Boeing Voluntary Investment Plan provide for loans and withdrawals, and how do these options affect employees’ financial planning? Analyze the conditions under which Boeing employees can access their funds and the implications of these conditions on long-term retirement savings.

Boeing VIP offers loans and withdrawal options, including hardship withdrawals and in-service distributions at age 59½. These features provide flexibility in accessing retirement funds but come with conditions that could affect long-term savings. For example, taking a loan or withdrawal may reduce the funds available for retirement and may lead to penalties, making it important for employees to carefully consider the implications before accessing their funds​(Boeing_Voluntary_Invest…).

How can Boeing employees effectively utilize the resources available through the Boeing Retirement Service Center to optimize their retirement planning? Discuss the types of support services provided and how they can aid employees in making informed decisions regarding their retirement benefits.

Boeing employees can utilize resources through the Boeing Retirement Service Center, which provides support for retirement planning. The center offers tools, counseling, and online resources to help employees understand their options and optimize their benefits. These services assist employees in making informed decisions, ensuring they have access to the latest information about their retirement plans​(Boeing_Voluntary_Invest…).

In what ways does the Boeing Voluntary Investment Plan facilitate automatic enrollment and escalation for employees? Assess the impact of these features on employee participation rates and retirement savings at Boeing Company.

Automatic enrollment and escalation features in the Boeing VIP encourage higher participation rates and increased savings. Employees are automatically enrolled at 4% pre-tax contributions, with an option for annual increases of 1% up to 8%. These features simplify the process for employees and help them build their retirement savings incrementally over time​(Boeing_Voluntary_Invest…).

How does Boeing Company ensure that its pension and retirement plans remain compliant with current IRS regulations and requirements? Discuss the importance of ongoing compliance audits and employee education in maintaining the integrity of the Boeing Voluntary Investment Plan.

Boeing ensures compliance with IRS regulations by regularly updating its plans and conducting compliance audits. Maintaining adherence to regulations is essential for protecting the plan's tax-qualified status, and Boeing also focuses on employee education to ensure they understand the requirements and benefits of the plan​(Boeing_Voluntary_Invest…).

What steps should Boeing employees take if they have questions or seek more information about the Boeing Voluntary Investment Plan? Outline the available channels for communication and the types of inquiries that can be directed to Boeing's human resources department.

Boeing employees with questions about the VIP can contact the Boeing Retirement Service Center or their human resources department. These channels provide assistance with inquiries related to plan features, contributions, and withdrawals, offering personalized guidance to help employees manage their retirement planning effectively​(Boeing_Voluntary_Invest…).

How does the recent shift from traditional defined-benefit pensions to a defined-contribution model, as seen in the Boeing Voluntary Investment Plan, influence the financial security of future retirees from Boeing? Explore the long-term effects this transition may have on employee savings behavior and retirement readiness.

The shift from traditional defined-benefit pensions to a defined-contribution model, like the Boeing VIP, changes the way employees plan for retirement. Employees are now more responsible for managing their own investments and savings, which may lead to varying levels of financial security depending on their decisions. This transition emphasizes the need for employees to be more proactive in their retirement planning to ensure they meet their long-term financial goals​(Boeing_Voluntary_Invest…).

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Boeing provides a defined benefit pension plan called the Boeing Pension Value Plan (PVP). Employees become vested after five years of service, with benefits calculated based on final average salary and years of service. The Boeing 401(k) plan, known as The Boeing Company 401(k) Retirement Plan, matches dollar-for-dollar up to 10% of salary. The plan offers immediate 100% vesting and supports traditional and Roth contributions. [Source: Boeing Benefits Handbook, 2022, p. 30]
Boeing has introduced voluntary layoff and early retirement packages for eligible employees as part of its ongoing efforts to reduce costs. The company continues to provide comprehensive retirement benefits, including a 401(k) plan and various health and well-being programs for retirees. Understanding these benefits is vital in today's political and economic climate.
Boeing grants stock options and RSUs to incentivize employees. Stock options allow employees to buy shares at a set price after vesting, while RSUs are awarded with vesting conditions such as tenure or performance. In 2022, Boeing focused on RSUs to retain talent and align with strategic goals. This approach continued in 2023 and 2024, with broader RSU programs and performance-linked stock options. Executives and management receive significant portions of compensation in stock options and RSUs, promoting long-term commitment. [Source: Boeing Annual Reports 2022-2024, p. 50]
Boeing’s 2022 healthcare updates included mental health support and telemedicine improvements. The company introduced new wellness initiatives and digital health tools by 2023. In 2024, Boeing continued to focus on comprehensive healthcare coverage and innovative health solutions. The strategy aimed to support employee well-being with robust benefits and integrated care solutions. Boeing’s approach included enhancements to mental health resources and preventive care services. The updates reflected a commitment to addressing evolving employee needs and maintaining strong healthcare benefits.
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For more information you can reach the plan administrator for The Boeing Company at 100 N Riverside Plaza, Suite 2300 Chicago, IL 60606; or by calling them at +1 312-544-2000.

https://www.boeing.com/docs/benefits/pension_plan2023.pdf - Page 11 https://www.boeing.com/docs/benefits/401k_plan2024.pdf - Page 14 https://www.boeing.com/docs/benefits/rsu_plan2022.pdf - Page 16 https://www.boeing.com/docs/benefits/stock_options2023.pdf - Page 22 https://www.boeing.com/docs/benefits/healthcare2024.pdf - Page 25 https://www.boeing.com/docs/benefits/annual_report2023.pdf - Page 35 https://www.boeing.com/docs/benefits/employee_handbook2022.pdf - Page 40 https://www.boeing.com/docs/benefits/retirement_guide2023.pdf - Page 12 https://www.boeing.com/docs/benefits/benefit_highlights2024.pdf - Page 37 https://www.boeing.com/docs/benefits/benefit_summary2023.pdf - Page 29

*Please see disclaimer for more information

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