Open Enrollment Essentials: Key Takeaways to Set Your Team Up for Success

Open enrollment season is a crucial time for HR professionals and business owners alike. Whether you're preparing for your first open enrollment or looking to streamline your process, a well-planned strategy can turn this annual task into a powerful opportunity to boost employee engagement, improve benefits communication, and ensure HR compliance.

In our recent DP Discover webinar, Open Enrollment Essentials: Setting Your Team Up for Success, HR expert Jessica Cook shared best practices to help companies navigate the open enrollment process with confidence and clarity.

What Is Open Enrollment?

Open enrollment is the designated period when employees can review, change, or enroll in their employee benefits, including:

• Medical, dental, and vision insurance

• Life and disability insurance

• Voluntary benefits like legal services or pet insurance

• Flexible Spending Accounts (FSAs) and Health Savings Accounts (HSAs)

Open enrollment is typically held in the fall to prepare for a January 1 renewal. The length varies by company, but generally lasts 1–4 weeks, depending on plan changes and employee size.

Why Early Planning Is Critical for a Smooth Open Enrollment Process

Starting early is one of the most important steps you can take to reduce stress and avoid last-minute issues.

Tips for early open enrollment planning:

• Review last year’s process to identify what worked and what didn’t.

• Survey employees to understand their benefits preferences and satisfaction levels.

• Evaluate your benefits offerings to ensure they are cost-effective, competitive, and relevant.

• Engage your benefits broker early to discuss renewal rates and possible carrier changes.

• Audit your HR technology to confirm your system supports digital benefits enrollment.

How to Communicate Employee Benefits Effectively

Clear, consistent, and engaging benefits communication is essential to a successful open enrollment.

Best practices include:

• Creating a communications timeline that includes emails, info sessions, and reminders

• Offering both digital and printed materials to support a multigenerational workforce

• Using simple language to explain complex terms like HDHPs, HSAs, and FSAs

• Highlighting major benefit changes like new carriers, coverage levels, or cost updates

Why Benefits Technology Is a Game-Changer

Outdated, manual enrollment processes increase the risk of errors and reduce employee confidence. That’s why investing in the right benefits technology platform is crucial.

Key benefits of using a digital enrollment system:

• Simplifies the employee benefits enrollment experience

• Reduces manual data entry and paperwork

• Enables carrier connections for seamless data transfers

• Supports self-service tools so employees can view and manage benefits year-round

Companies can also integrate decision support tools, allowing employees to compare plans based on their life circumstances, leading to more informed choices and fewer follow-up questions.

How to Support All Employees During Open Enrollment

With four (or more) generations in the workforce, HR teams must design an inclusive open enrollment experience that meets diverse needs and tech capabilities.

Suggestions:

• Offer personalized support sessions for employees who prefer hands-on assistance

• Use screen-sharing tools or phone calls for remote employees

• Provide recorded webinars, guides, and FAQs for on-demand learning

• Include paper-based alternatives for those who need them

Common Open Enrollment Mistakes to Avoid

To run an effective open enrollment, watch out for these common pitfalls:

• Rushing the process due to late carrier renewals

• Unclear communication filled with jargon or inconsistent messaging

• Missed deadlines that result in delayed insurance cards or coverage

• Low employee engagement caused by treating open enrollment as a one-time event

• Manual processes that lead to errors and HR frustration

Remember: Open enrollment is not just a compliance requirement, it’s a strategic opportunity to reinforce your company’s employee value proposition.

Don’t Forget Post-Open Enrollment Strategies

The work doesn’t stop once open enrollment closes. Strong follow-through ensures employees understand and utilize their benefits.

Post-enrollment best practices:

• Confirm employees receive insurance ID cards and debit cards for FSAs/HSAs

• Communicate any back-end changes that might affect plan usage

• Continue educating employees on how to use their benefits year-round

• Set up a system for handling life event changes (birth, marriage, etc.)

• Regularly audit carrier bills to ensure correct coverage and payroll deductions

Compliance doesn't end either, stay on top of changing federal and state regulations to avoid costly penalties.

Final Thoughts: Make Open Enrollment a Strategic Win

As Jessica shared in the webinar, “Open enrollment isn’t just a box to check—it’s a chance to support your team, reinforce your culture, and show your employees that their well-being matters.”

Looking to upgrade your open enrollment strategy, improve benefits administration, or explore HR technology solutions? Dominion Payroll is here to help!