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How Windstream Holdings Retirees Are Using AI to Simplify Everyday Life

'Artificial intelligence is helping many Windstream Holdings employees simplify their transition into retirement by organizing finances and daily routines, but the key is to use these tools as support—not substitution—for thoughtful planning and professional guidance.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'Windstream Holdings employees are finding that AI can streamline everything from budgeting to wellness, but lasting success in retirement comes from combining technology’s efficiency with informed financial decision-making.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How artificial intelligence (AI) is helping Windstream Holdings retirees simplify daily life and handle complex tasks.
The ways AI can enhance health, home, and financial organization in retirement.
Why retirees are increasingly confident using AI to boost efficiency and reclaim valuable time.

Many Windstream Holdings retirees are discovering that slowing down isn’t always easy, despite looking for respite from decades of early mornings, complex undertakings, and global operations. Handling investments, planning vacations, and staying organized can still feel demanding during retirement.

That’s where artificial intelligence (AI) has stepped in. What once seemed futuristic is now a practical tool for Windstream Holdings’s retired professionals who want to streamline routines and reclaim valuable time.

According to Wealth Enhancement financial planner Kevin Won, CFP®, AWMA®, CRPC®, “we’re seeing older adults experimenting with AI tools for efficiency. They understand that these tools can help them reclaim time, which is one of life’s most precious resources.”

Simplifying Complex Tasks

While still in the workforce, AI is helping Windstream Holdings employees transform their daily workflow. Tasks that once took hours—such as reviewing financial reports or tracking industry or market data—now take minutes with the help of AI assistants that can summarize data, highlight key performance trends, and draft personal reports.

Others are using AI to enhance their personal lives. For instance, with an AI-powered trip planner, it's possible to enter your preferred travel destinations, dates, and hobbies, and have the chatbot design an itinerary for you complete with dining, sightseeing, and activity suggestions.

The same is true after retirement. “The retirees I work with value how AI brings order and clarity,” Won adds. “Whether it’s comparing health care options or managing monthly expenses, these tools can handle the heavy lifting so retirees can focus on other areas of their lives.”

Improving Health and Home Management

Many former Windstream Holdings professionals are also turning to AI for personal wellness and home organization. Some use chatbots for home maintenance guidance, while others leverage AI to build custom workout plans that adapt to travel schedules or physical limitations. These tools help retirees maintain consistency without needing advanced tech skills or expensive memberships.

According to Won, “AI can give older adults autonomy. They don’t need to wait for instruction or assistance. Technology enables them to take the lead in their daily lives, including finances and health care choices.”

A Modern Assistant for Financial Confidence

Retirees can also use AI to help arrange their financial information before meetings with advisors. From summarizing financial articles to preparing questions, AI helps retirees save time while staying informed. Some even use it as a digital filing assistant, categorizing tax documents, receipts, and travel logs for the upcoming year.

Won cautions, however, that “AI should be viewed as guidance, not a promise. It’s a powerful assistant, but it can still make errors—especially on topics like health or finance—so always double-check important information.”

From Skepticism to Confidence

While some retirees were initially hesitant to adopt AI, many have now incorporated it into their routines. Surveys show that, while older generations are slower to adopt new technologies, comfort and usage are steadily rising.¹

Won explains, “Retirees who’ve spent decades adapting to innovation in corporate environments, like Windstream Holdings, already have the resilience and mindset needed to learn new tools. Now, AI works for them—reducing complexity, not adding to it.”

A Smart Way to Simplify Retirement

For many retirees, using AI is about boosting productivity, not just curiosity. Automating travel planning, organizing budgets, and reducing decision fatigue can make retirement more manageable and less stressful.

According to Won, “you’re really adding peace of mind when you integrate smart tools into daily life. The goal isn’t to master the technology. It’s to let it operate behind the scenes so you can focus on what matters most.”

If you’re a Windstream Holdings retiree looking to organize your finances, streamline health care costs, or enjoy your retirement with fewer hassles, The Retirement Group can help. Call (800) 900-5867 to speak with a knowledgeable representative today.

For more information, visit WealthEnhancement.com or call Wealth Enhancement Group at (800) 492-1222 to speak with a Certified Financial Planner.

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Sources:

1. Kakulla, Brittne, Laura Skufca, Patty David, Jessica Boothe, and Kristen Garrett. ' Empowering Independence With Technology Among Adults Age 50-Plus .' Washington, DC: AARP Research, Jan. 2025.
2. “Young Adults Are Leading the Way in AI Adoption.” AP-NORC Center for Public Affairs Research, 29 July 2025.
3. Chui, Michael, et al. The Economic Potential of Generative AI: The Next Productivity Frontier. McKinsey Global Institute, June 2023.
4. Chatbots in Consumer Finance. Consumer Financial Protection Bureau, June 2023.
5. “Older Adults Express Mixed Views on Artificial Intelligence.” NORC at the University of Chicago, Oct. 2023.

What are the implications of the Windstream Pension Plan for employees who wish to retire early, specifically regarding the eligibility criteria and benefit calculations that will affect their financial planning? How does Windstream address concerns for employees who may be contemplating retirement before reaching the defined Normal Retirement Age of 65?

Early Retirement and Financial Planning: Employees may retire early at age 55 with 20 or more years of service, though the pension benefit will be reduced. The reduction is by 1/180th for the first 60 months and 1/360th for each of the next 60 months that commencement precedes the normal retirement date of age 65. This ensures early retirees can still receive benefits, though at a lower amount than if they had waited until age 65(Windstream_Pension_Plan…).

In what ways does the Windstream Pension Plan protect the interests of employees during a potential plan termination? Specifically, how does the plan ensure that accrued benefits are preserved and what procedures are in place to inform employees about their rights under the Employee Retirement Income Security Act of 1974 (ERISA)?

Plan Termination Protections: In the event of plan termination, Windstream ensures all accrued pensions are fully vested. The plan assets will be used exclusively to meet accrued pension obligations before any surplus may revert to the company. Participants are also protected by the Pension Benefit Guaranty Corporation (PBGC), which guarantees most pension benefits(Windstream_Pension_Plan…).

How does Windstream determine the necessary contributions to the Pension Plan, and what role does an independent actuarial assessment play in this process? Additionally, how does this funding approach impact the overall financial stability of the Windstream Pension Plan and the benefits it promises to its participants?

Contribution Determination and Actuarial Role: Windstream’s contributions to the pension plan are determined by an independent actuary who evaluates the plan annually to recommend adjustments based on experience. This approach ensures that the plan remains financially stable and capable of meeting its promised benefits(Windstream_Pension_Plan…).

What options are available to employees of Windstream regarding the forms of pension benefit payouts upon retirement, and how do these options like the Joint and Survivor Annuities differ in terms of financial implications for both the retiring employee and their spouse?

Benefit Payout Options: Windstream offers several pension payout options, including Joint and 100% Survivor Annuity, Joint and 50% Survivor Annuity, and a 10-Year Certain and Life Annuity. These options differ in terms of the benefit reduction applied to ensure payments continue for the life of the spouse, impacting both the retiree’s and the spouse’s financial planning(Windstream_Pension_Plan…).

How should Windstream employees approach the process of claiming pension benefits, especially if their claims have been denied? What recourse is available for employees who are facing issues with their pension claim and wish to understand their rights and the appeal process?

Claiming Pension Benefits and Denied Claims: If an employee's pension claim is denied, they will receive a written notice explaining the reasons for the denial and the specific plan provisions involved. Employees may appeal the decision within 60 days, and the appeal process must be completed within 60 days of the request, with the right to file a civil lawsuit if necessary(Windstream_Pension_Plan…).

Given the frozen status of the Windstream Pension Plan, what should employees understand about their service years and how these years contribute to their pension benefits? How does Windstream communicate these rules to ensure clarity among its employees?

Service Years and Frozen Status: Since the Windstream Pension Plan is frozen, no additional benefits accrue after December 31, 2007. However, employees continue to earn years of service, which count toward eligibility for early retirement and vesting. Windstream provides clear communication through its summary plan description and resources to ensure employees understand these rules(Windstream_Pension_Plan…).

What strategies can Windstream employees employ to maximize their pension benefits and ensure they are making informed decisions about their retirement? How does Windstream support its employees in accessing the necessary resources and information to facilitate effective retirement planning?

Maximizing Pension Benefits: Employees are encouraged to consider their timing of retirement carefully, as delaying retirement closer to the normal retirement age of 65 reduces benefit reductions. Windstream supports retirement planning through its pension resources and access to Merrill Service Representatives who can assist with planning tools(Windstream_Pension_Plan…).

How does Windstream ensure that employees are aware of their obligations under the plan regarding the filing of claims and maintaining updated personal information? What measures does the company take to keep communication channels open for any inquiries or updates employees might need?

Maintaining Updated Information: Windstream emphasizes the importance of keeping personal information up to date, including changes to contact information. Employees are responsible for filing claims in a timely manner, and failure to do so may result in delays or forfeiture of benefits(Windstream_Pension_Plan…).

In the event of the death of a vested Windstream employee, what benefits are guaranteed to eligible spouses under the plan, and how do survivors initiate the process for claiming these benefits? What steps should surviving spouses take to ensure they receive the necessary support and information from Windstream?

Survivor Benefits and Claim Process: In the event of the death of a vested employee, the spouse is entitled to receive a pre-retirement survivor annuity, which may start on or after the employee’s earliest retirement age. The spouse must contact Windstream to initiate the claim process and may receive a lump sum if the benefit’s present value is below certain thresholds(Windstream_Pension_Plan…).

How can Windstream employees reach out to the companyâ€™s Benefits Committee or Plan Administrator for detailed inquiries about their pension benefits? What contact methods are available, and what information should employees prepare to facilitate effective communication regarding their pension inquiries? These questions will help employees navigate the complexities of the Windstream Pension Plan and ensure they are well-informed as they approach retirement.

Reaching the Benefits Committee: Windstream employees can contact the Benefits Committee or Plan Administrator at Windstream Services, LLC in Little Rock, Arkansas, or via the Merrill Service Center at 1-800-228-4015. Employees should have relevant information, such as personal and employment details, ready to facilitate efficient communication(Windstream_Pension_Plan…).