When it comes to employee health benefits, timing is everything—which is why understanding what small business owners need to know about open enrollment is so important. This annual window determines when your employees can sign up for or make changes to their health insurance coverage, and missing key dates can leave your team without benefits for the year ahead.
By knowing the deadlines, preparing early, and communicating clearly, you can turn open enrollment from a stressful scramble into a streamlined process that supports both your employees and your business.
Health Insurance Enrollment Period
Staying on top of open enrollment deadlines is crucial for small business owners. Missing a date could mean your employees go without coverage until next year. Here’s the timeline to keep in mind:
- November 1, 2025: Open enrollment begins.
- December 15, 2025: Last day to apply for or change plans that start on January 1, 2026.
- January 1, 2026: Plan coverage starts for those who applied and finalized their plans by December 15.
- January 15, 2026: Last day to enroll in coverage.
- February 1, 2026: Plan coverage starts for those who applied between December 15, 2025 and January 15, 2026.
By planning ahead and following best practices during and after enrollment, you can avoid last-minute stress, keep your team informed, and ensure there’s no gap in benefits.
Early Open Enrollment Preparation
By starting open enrollment efforts early, employers have enough time to inform and educate workers about their benefits and what the health plan options actually mean.
Tailoring Offerings
Employee health insurance can serve as a powerful attraction and retention tool. However, that’s only true if workers see value in these offerings. That’s why employers should tailor their health insurance options to include perks employees care about ahead of open enrollment.
Employers should keep in mind that employee health insurance is one of the top reasons employees join companies and stay at their jobs. That’s why it’s critical for employers to seriously consider speaking with employees about what provides the most value for their unique circumstances. Adding or tweaking a few options could be the difference between retaining and losing top performers.
Also, gaining employee feedback ahead of open enrollment shows a meaningful interest in their concerns. With a good pulse on workers’ needs, this intel can also impact employee attraction efforts.
Determining Key Messaging
After solidifying health insurance options, employers need to plan their messaging and communication strategies. For 2026, key messaging might focus on new or updated benefits offerings.
Putting benefits front and center can compel employees to weigh the advantages of searching for new jobs against guaranteed perks. Employers should detail their offerings so employees understand everything they could potentially lose by changing jobs. Touching on these details is particularly important, considering many workers don’t fully understand the health insurance benefits they elected during open enrollment. This means some employees may be job hunting for perks that they already have access to.
As employees’ needs vary, outlining the different health insurance offerings can help them understand which benefits they need and will likely use. Employees’ appreciation for benefits may improve when they can choose plans tailored to their specific needs. The more appreciative employees are, the less likely they are to seek other job opportunities.
Communicating Employee Benefits
Ultimately, employers must spread the word about open enrollment and their offerings. Countless surveys show that employees want more help understanding their options. This means an open enrollment communication plan needs to start early, provide ample educational resources, and have multiple channels.
An effective open enrollment communication strategy may include the following components:
- Group meetings to discuss available benefits
- One-on-one meetings to go over any questions
- Multichannel communication methods (e.g., videos, printouts, guides, presentations, emails, and comprehensive guides)
- Periodic enrollment reminders, including enrollment dates and workplace-specific instructions
- Messaging that directs employees to designated points of contact for questions (e.g., HR)
Leveraging technology allows employers to communicate more frequently and effectively with employees. With more employees working remotely, virtual enrollment may be the most feasible option for many employers, saving them time and resources.
Early open enrollment communication gives employees more time to understand their options. Although year-round communication is ideal, employers can amp it up for open enrollment. A better understanding of offerings may help employees make more active choices in their health plans during the open enrollment season and beyond by helping them understand the perks of staying with the organization.
Open Enrollment Period Actions
Open enrollment can still feel overwhelming for employees—no matter how much preparation you’ve done. To make the process smoother, consider having a benefits expert or HR representative available to answer questions and provide clarity. Encourage managers to regularly check in with their teams so no one feels lost or rushed.
This is the time to distribute all essential materials, such as the enrollment schedule, key deadlines, statements of current coverage, details on plan changes and rates, summaries of benefits, the open enrollment guide, necessary forms, and any organization-specific information.
Clear communication is key. Set reasonable internal deadlines ahead of the official ones and send regular reminders—especially as the final dates approach. This kind of guidance not only keeps employees on track but also ensures your team feels supported and confident when making coverage decisions.
Open Enrollment Notice
Speaking of clear communication, small businesses should provide certain benefit notices to their employees in connection with their plans’ open enrollment periods. Some of these notices must be provided at open enrollment time, such as the Summary of Benefits and Coverage (SBC).
Other notices, such as the Women’s Health and Cancer Rights Act (WHCRA) notice, must be distributed annually. Although these annual notices may be provided at different times throughout the year, employers often choose to include them in their open enrollment materials for administrative convenience. Some of these notices may be included in the plan’s Summary Plan Description (SPD) or detailed benefits summary provided by a health insurance issuer or third-party administrator (TPA).
In addition, employers should review their open enrollment materials to confirm that they accurately reflect the terms and cost of coverage. In general, any plan design changes for 2026 should be communicated to plan participants either through an updated SPD or a Summary of Material Modifications (SMM).
Post-Enrollment Duties
The weeks that follow are critical for making sure your employees’ coverage starts smoothly and without surprises. Here’s how to wrap up open enrollment the right way:
Double-Check Enrollment Details
Before sending anything off, review every enrollment form for accuracy and completion. Look for missing information, typos, or unclear entries. Catching errors now can prevent frustrating delays and costly mistakes later.
Submit to Your Carrier Promptly
Once everything is verified, send the finalized forms to your health insurance carrier as soon as possible. Quick submission helps ensure coverage is activated on time, so employees can use their benefits when they need them.
Confirm Compliance
Review your benefits plan to ensure it meets all current health care reform requirements. Staying compliant not only protects your business but also safeguards employee access to benefits.
Check on ID Cards
Follow up to make sure employees receive their insurance ID cards. If someone’s card hasn’t arrived, contact the carrier to resolve the issue promptly.
Address Remaining Questions
Even after enrollment, employees may have questions about their coverage. Take the time to connect with them, provide clarity, and confirm they understand how to use their benefits.
By following these steps, you’ll help your employees feel confident in their coverage—and keep your business running smoothly in the process.
At the end of the day, what small business owners need to know about open enrollment is that success comes down to preparation, communication, and follow-through. When you stay ahead of deadlines, tailor your benefits to your employees’ needs, and provide clear guidance, you not only keep your business compliant but also show your team that you value their well-being.
If you’d like expert guidance to make the process even easier, consider partnering with a trusted benefits advisor—they can help you navigate regulations, avoid costly mistakes, and ensure your employees feel informed and confident in their coverage choices.
Please let us know if you have any questions. We understand that local companies have unique needs that most national firms don’t consider or struggle to identify. This leaves your people with a less effective, one-size-fits-all benefits plan. However, our ability to cater to the needs of our clients comes from decades of client partnerships. This perspective allows us to fully address unique needs and generate creative benefits plans.
You shouldn’t have to worry about just being a number, offering a generic plan, or getting the unique support you need. Call us today.
This Benefits Insights is not intended to be exhaustive nor should any discussion or opinions be construed as professional advice.