New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

How Five Below Retirees Are Using AI to Simplify Everyday Life

Healthcare Provider Update: Healthcare Provider for Five Below Five Below, a popular retail chain that focuses on selling a variety of items priced at $5 and below, utilizes Aetna as their healthcare provider. This partnership enables employees to access a range of health insurance plans and benefits that support their wellness needs. Potential Healthcare Cost Increases in 2026 As the healthcare landscape shifts, significant premium hikes are anticipated in 2026, particularly for those enrolled in Affordable Care Act (ACA) marketplace plans. With some states projecting increases exceeding 60%, the absence of enhanced federal premium subsidies will exacerbate this situation, potentially raising out-of-pocket premium costs by over 75% for most enrollees. This financial strain-coupled with ongoing medical cost inflation-could jeopardize access to affordable healthcare for millions of Americans, especially those with chronic conditions who rely on comprehensive coverage. Click here to learn more

'Artificial intelligence is helping many Five Below 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.

'Five Below 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 Five Below 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 Five Below 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 Five Below’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 Five Below 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 Five Below 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 Five Below, 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 Five Below 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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Articles you may find interesting:

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 type of retirement savings plan does Five Below offer to its employees?

Five Below offers a 401(k) retirement savings plan to its employees.

Is participation in the 401(k) plan at Five Below mandatory?

No, participation in the 401(k) plan at Five Below is voluntary for employees.

Does Five Below provide any matching contributions to the 401(k) plan?

Yes, Five Below offers matching contributions to eligible employees who participate in the 401(k) plan.

At what age can employees at Five Below start contributing to the 401(k) plan?

Employees at Five Below can start contributing to the 401(k) plan as soon as they meet the eligibility requirements, typically at age 18.

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

Employees at Five Below can enroll in the 401(k) plan by completing the enrollment process through the company’s HR portal.

What investment options are available in the Five Below 401(k) plan?

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

Can employees at Five Below change their contribution percentage to the 401(k) plan?

Yes, employees at Five Below can change their contribution percentage at any time, subject to plan rules.

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

Five Below has a vesting schedule that typically requires employees to work for a certain number of years before they fully own the matching contributions.

How often can Five Below employees review their 401(k) account statements?

Employees at Five Below can review their 401(k) account statements quarterly or online at any time through the plan’s website.

What happens to the 401(k) plan if an employee leaves Five Below?

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

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

For Five Below, the company offers a 401(k) plan but does not provide a traditional pension plan. The 401(k) plan at Five Below includes several key features: Eligibility: Employees must be at least 21 years old to participate. Enrollment in the plan can occur after the first paycheck, with deferrals starting on January 1st or July 1st following the hire date. Employees become eligible for the employer match once they begin deferring contributions. Contributions: Employees can contribute on a pre-tax or after-tax (Roth) basis, up to the IRS annual limits. For 2022, the maximum employee contribution was $20,500, and it increased to $22,500 in 2023. Employees aged 50 and older can make catch-up contributions, with limits of $6,500 in 2022 and $7,500 in 2023. The company offers a match of 100% on the first 4% of eligible contributions and 50% on the next 2%. Vesting: Employees are immediately vested in all 401(k) contributions and any earnings from these contributions.

Restructuring Layoffs and Benefits Changes: Five Below has been focusing on optimizing its workforce as part of a broader strategy to maintain its competitive edge in the retail market. This has included targeted layoffs aimed at streamlining operations, particularly in underperforming locations. The company has also been reviewing its employee benefit structures, including adjustments to retirement plans to better align with current economic conditions. These changes are part of a proactive approach to manage costs while continuing to invest in growth areas like e-commerce.

Company Name: Five Below Stock Options and RSUs Available: Five Below offers stock options and RSUs to eligible employees, including executives and senior management. The RSUs are granted based on performance and tenure. Eligibility: Five Below typically awards stock options and RSUs to high-performing employees and those in key positions. Employees must meet certain performance metrics and tenure requirements to qualify. Company Name: Five Below Stock Options and RSUs for 2022: In 2022, Five Below granted stock options and RSUs to various employees, focusing on those who significantly contributed to the company's growth. The vesting schedule for RSUs is often tied to continued employment over a few years. Source: [Five Below 2022 Annual Report, Page 58] Company Name: Five Below Stock Options and RSUs for 2023 and 2024: For 2023 and 2024, Five Below continued offering stock options and RSUs, with increased emphasis on aligning employee incentives with company performance. The specific terms of these grants were detailed in their annual filings and shareholder communications. Source: [Five Below 2023 Proxy Statement, Page 42]; [Five Below 2024 Annual Report, Page 65] Sources: Five Below 2022 Annual Report, Page 58 Five Below 2023 Proxy Statement, Page 42 Five Below 2024 Annual Report, Page 65

Five Below offers a range of health benefits to its employees, tailored to different needs and employment statuses. Full-time employees can choose from multiple health plans, including High Deductible Health Plans (HDHP) and Exclusive Provider Organization (EPO) plans, each with varying levels of coverage and copays. For example, the EPO plan now features reduced copays, with visits to primary care doctors costing $20 and specialist visits $40. There is also an emphasis on preventive care, with certain plans covering preventive services at 100%. Additionally, Five Below provides access to telemedicine services through CirrusMD, which allows employees to consult with physicians 24/7 via secure video chat or phone. This is part of their partnership with Cigna, which also includes pharmacy benefits. The company has introduced new wellness initiatives like Wellbeats, which offers on-demand workouts, mental health classes, and nutrition education.

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For more information you can reach the plan administrator for Five Below at , ; or by calling them at .

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