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.
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.
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.
Clear, consistent, and engaging benefits communication is essential to a successful open enrollment.
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
Outdated, manual enrollment processes increase the risk of errors and reduce employee confidence.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.
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
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.
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.
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!