6 Strategies for a Successful Open Enrollment 2025

Open enrollment is right around the corner, and with it comes a strategic opportunity to educate employees on their benefits, connect them to wellness resources, and guide them in making informed choices that support their health and well-being in the year ahead. While the season can be filled with employee questions, administrative tasks, and looming deadlines, there are intentional strategies organizations can use to streamline the process and ensure open enrollment is smooth and impactful.

How Does Open Enrollment Work?

Open enrollment is the once-a-year window during which employees can review, select, or update their benefit options for the upcoming plan year. During this period, HR teams share enrollment resources, answer benefit plan questions, and use digital platforms to make the selection process easier. Once selections are finalized, they remain in place for the full year unless an employee qualifies for a Special Enrollment Period (SEP) due to a major life event.

When Is Open Enrollment for Health Benefits in 2025?

For employer-sponsored health plans, the open enrollment period is set by the company, not the government. While timelines vary, most companies hold their enrollment for a two- to four-week period in the fall (typically October or November) for plans beginning on January 1. For example, open enrollment could run from November 1, 2025, through November 30, 2025, and selections made during this time would become active on January 1, 2026.

Separately, for individuals who buy insurance on their own through the Affordable Care Act (ACA) Marketplace, the federal open enrollment period for 2026 coverage runs from November 1, 2025, through January 15, 2026. Several states that run their own marketplaces have different deadlines. If you provide guidance to individuals who are not covered by your organization, it’s important to clearly communicate these exceptions.

States with alternative open enrollment periods for individual coverage through the Affordable Care Act (ACA) Marketplace include:

• Idaho: October 15, 2025 – December 16, 2025  
• California: November 1, 2025 – January 31, 2026  
• New Jersey: November 1, 2025 – January 31, 2026  
• New York: November 1, 2025 – January 31, 2026  
• Rhode Island: November 1, 2025 – January 31, 2026 
• Massachusetts: November 1, 2025 – January 23, 2026  
• Maryland: November 1, 2025 – January 15, 2026  
• Maine: November 1, 2025 – January 15, 2026  
• Minnesota: November 1, 2025 – January 15, 2026  
• Virginia: November 1, 2025 – January 15, 2026  
• Washington, D.C.: November 1, 2025 – January 31, 2026

Special Enrollment Periods

Outside of the standard employer-determined open enrollment window, employees may still adjust their benefits if they experience a qualifying life event, such as marriage, divorce, the birth or adoption of a child, or loss of other coverage. These SEPs ensure that employees can update their health coverage when major life changes occur, helping them and their families stay protected without waiting for the next annual cycle.

Why Is Employee Engagement during Open Enrollment Important?

Open enrollment is one of the most influential times of the year for employee well-being, as benefits are a cornerstone of the employee experience and have a direct impact on health outcomes. According to Glassdoor, 60% of employees consider benefits to be a main factor when deciding to accept a job. MetLife’s research further highlights their importance, finding that half of employees say workplace benefits ease concerns about unexpected health and financial challenges, and 70% say that customizable benefits would increase their loyalty to their companies. 

Because benefits have such a strong influence on employee attraction and loyalty, it’s critical that employees feel prepared and supported to make the most of the open enrollment period. The decisions employees make during this time affect their health, finances, and peace of mind for the year ahead.  

Open enrollment is the primary opportunity to clearly communicate what benefits are available, how plan changes may affect employees, and which options best support their unique needs. Engaged employees are more likely to explore their choices, from health insurance and retirement savings to wellness programs and Lifestyle Spending Accounts (LSAs), and maximize the resources available to them. 

On the other hand, if employees aren’t properly educated, they could miss the enrollment window or misunderstand their benefits, which could mean losing benefit access or forgoing cost-saving opportunities until the next enrollment cycle. By encouraging active participation and educating employees on their benefit options, HR teams can improve benefits utilization while strengthening employee trust, satisfaction, and well-being.

6 Strategies for Successful Open Enrollment

1. Communicate Key Dates and Changes

Clear, consistent communication is the foundation of a smooth and successful open enrollment. Employees are often overwhelmed by complex plan documents, deadlines, and terminology, which can lead to confusion, missed opportunities, or rushed decisions. By proactively delivering information in digestible formats and across multiple channels, HR teams can reduce stress, build trust, and empower employees to make confident choices about their health and financial well-being.  

Best Practices for Benefits Communication  

• Start messaging 8 to 12 weeks before enrollment begins. 
• Use multiple channels (e.g., email, intranet posts, flyers, team meetings) to ensure information reaches everyone. 
• Highlight important deadlines multiple times and continue to send reminders throughout the enrollment window.  
• Be clear about plan changes, premium adjustments, deductible shifts, or new benefit offerings, so employees have time to evaluate their options.  
• Tailor your outreach to on-site, hybrid, and remote employee groups so all receive the details they need in a format that best reaches them. 

2. Promote Underutilized Benefits

While it’s crucial to communicate benefits that require enrollment, this is an ideal time to give a comprehensive view of all benefits offered, so employees are educated and empowered to engage year-round.

Benefits like student loan and tuition reimbursement, disability insurance, HSAs, commuter benefits, and mental health resources often go unused because employees either don’t know they exist or don’t know how to access them. In fact, according to Prudential Financial research, nearly 60% of employers offer mental health support in the form of EAPs, but only 31% of employees have actually used this benefit. Among employees who use these programs, 69% report being highly satisfied, highlighting a prominent opportunity to better support workforce mental health.

Tips for Promoting Underutilized Benefits

• Create benefit spotlights: Dedicate part of your open enrollment materials (e.g., emails, flyers, webinars) to lesser-known benefits, explaining how they work, who is eligible, and whether or not they require enrollment.
• Use real-life examples: Share short employee stories or scenarios (an HSA helping with unexpected expenses or tuition reimbursement funding career growth) to make benefits more relatable. 
• Simplify access instructions: Provide clear, step-by-step guidance on how to use each benefit and link directly to log-in portals, claim forms, or vendor support pages in digital communications.
• Keep messaging going year-round: Reinforce awareness after open enrollment with quarterly reminders, manager talking points, or seasonal campaigns (e.g., commuter benefits in winter, EAP during Mental Health Awareness Month).
• Tailor communication by audience: Highlight different benefits for different groups. Early-career employees may value student loan support, while mid-career employees may prioritize HSAs, retirement accounts, or disability coverage.

3. Leverage Technology

Digital tools streamline the enrollment experience and help to reduce confusion. Use intranets, employee portals, or a benefits navigation hub to centralize documents, FAQs, and guides, or invest in a platform that has a more robust solution for benefits enrollment and management. For non-desk or frontline workers, prioritize mobile-friendly platforms so that resources are easy to access from wherever they work. The right technology simplifies enrollment and reinforces transparency and accessibility. 

Below is an at-a-glance comparison of some of the top platforms that support benefits enrollment, management, and navigation.

4. Offer Personalized Support

Even with clear communication and digital tools, many employees still need one-on-one guidance to feel confident in their benefits decisions. Offer personalized support through HR office hours, virtual Q&A sessions, or one-on-one consultations with benefits specialists. This gives employees an opportunity to receive guidance on specific topics such as comparing family coverage options, understanding out-of-pocket costs, or exploring how a Health Savings Account (HSA) fits into their long-term financial planning. Personalized touchpoints build employer trust and reduce the risk of costly mistakes, ensuring employees select benefits that truly meet their needs.

For organizations with large or distributed workforces, AI-powered chatbots, like Flimp’s Employee Benefits AI Agent, Espressive’s BaristaGPT, Leena AI, or Moveworks’ AI Assistant,  can transform the open enrollment experience by providing employees with on-demand, personalized support. Available 24/7, these tools are especially valuable for teams working across time zones or outside standard office hours. By handling routine questions and simplifying navigation, chatbots reduce the strain on HR teams while offering tailored benefits guidance based on employee profiles or past inquiries.

5. Host a Health Fair

A health fair is an interactive event that gives employees access to valuable wellness resources and clear, practical education on workplace benefits, creating powerful opportunities to boost engagement during open enrollment. By bringing benefits providers and wellness experts together (whether virtually or in person), health fairs create space for meaningful interaction and education.

Successful health fairs often include sessions on topics like mental health and financial investing education, as well as information on health plan offerings, continuous wellness programs, and other high-value benefits that help employees see the full scope of support available to them. Beyond showcasing specific programs, these events reinforce how benefits connect to overall well-being, empowering employees to make confident, informed choices during open enrollment and beyond.

6. Conduct Post-Enrollment Follow-Ups

The weeks and months that follow open enrollment are critical for reinforcing benefits education and ensuring employees feel supported as they begin to use their selections. Without consistent follow-up, employees may forget deadlines, underutilize resources, or feel unsure about where to go for help. Creating a post-enrollment follow-up plan shows employees that you’re invested in their ongoing health and well-being rather than checking a compliance box. 

Tips for Effective Follow-Up

• Send timely reminders: Highlight key dates like FSA and HSA contribution deadlines, preventive care checkups, or windows for updating dependent information.  
• Promote benefits utilization: Share tips and quick guides on how to make the most of programs such as EAPs, LSAs, commuter benefits, or telehealth services to keep these resources top of mind. 
• Gather employee feedback: Use short surveys or pulse checks to learn how employees experienced the enrollment process, where communication fell short, and what resources would make next year smoother. 
• Close the loop with leadership: Share survey results and enrollment insights with leaders to adjust communication strategies, streamline processes, and better align benefits with employee needs in future cycles.