A Guide for SMBs to Survive (and Thrive) During 2026 Open Enrollment

Open enrollment is the annual period when employees can enroll in, change, or decline their employer-sponsored benefits (most commonly health insurance, dental and vision coverage, life insurance, disability plans, and retirement savings options). For most U.S. businesses, this process takes place in the final quarter of the year, ahead of January 1 plan renewals.

It is one of the most intense seasons for HR. 

Although it might be tempting to rush and see it as “mere admin”, the decisions made during this period affect employers and employees alike:

• For employers, it is one of those “moments that matter” that reinforce employee trust, support informed decision-making, and position the company’s benefits offering as a reflection of its values and culture. A well-run enrollment cycle improves engagement, boosts retention, and strengthens internal credibility for HR.

• For employees, it is a time of making choices that will affect their mental, physical, and financial well-being, as well as their families.

However, data shows that 70% of employees spend 30 minutes or less reviewing their benefits during open enrollment. The result? Most keep their previous selections or go to social media for advice. The risk is accessing incomplete or misleading information (and making the wrong decisions).

In this post, we will deep dive into the main challenges HR will face this year, outline a step-by-step strategy to help you educate employees and improve benefit navigation, and offer an open enrollment checklist to stay organized and reduce workload. 

Why This Year Will Be More Challenging

• Rising Costs: With 77% of employees concerned about rising medical costs, inflation, and general economic uncertainty, HR will be flooded with inquiries (ACA plans have risen by 26% on average, with some states seeing 30% increases). 
• Benefits Information Is Becoming More Complex: Almost 4 in 10 employees struggle to understand employers’ communications around benefits and open enrollment, up 6 percentage points from last year. 
• SMBs Limited Capacity: For SMBs managing open enrollment, access to advanced, AI-powered HR platforms will become critical to confirm benefit options, track engagement and utilization, and manage audits.
• Compliance Deadlines and Overload: Employers must update plan documents and deliver notices such as the Summary of Benefits and Coverage (SBC), Medicare Part D disclosure, HIPAA privacy notice, and COBRA continuation coverage. For small HR teams, these layered requirements compete with other year-end responsibilities.

How to Lead a Successful Open Enrollment Season

Open enrollment is more than helping employees select a plan. It starts by understanding their unique needs and what people weigh when reviewing benefits. 

There are some trends: Gen Z employees prioritize paid leave and mental health support; Millennials may pay special attention to child and elder care, and Boomers often focus on medical and retirement. However, today, people expect more holistic support. Think of disability insurance and pet insurance. Or even legal assistance and workplace violence coverage, addressing a growing organizational risk. Orchestrating the right mix of benefits increases utilization. And if people have a positive experience, they are 2.4× more likely to feel holistically healthy and 1.8× more likely to trust their employer’s leadership. 

So think of benefits as a tool to show you really care for people, but also as a tool for talent retention and engagement.  In this section, we outline six steps to make your enrollment cycle seamless and impactful, and provide a comprehensive checklist to ensure nothing falls through the cracks. 

1. Align Benefits with Company Goals and Employee Needs

Before launching timelines or communications, step back and assess: Are our benefits aligned with your workforce's current needs and the business priorities?

Start this review 8–12 weeks before open enrollment to ensure enough time for plan design, vendor negotiations, and internal coordination:

• Survey employees to learn which improvements they want most.
• Use claims data, satisfaction metrics, and utilization trends to guide plan selection
• Reassess contribution strategies to balance affordability with financial control
• Consider non-traditional benefits like emergency savings or financial wellness tools

2. Adjust Communication Using Multiple Channels

When designing your communication strategy, consider that employees consume information in different ways. Using multiple channels not only increases reach—it also improves the chances that people will engage with their benefits, understand them, and take action. A mix of formats allows employees to revisit key information and ask questions in the ways they’re most comfortable with.

Begin outlining your communication plan 8–10 weeks before open enrollment begins. Include audience segmentation, key messages, and delivery channels. Avoid one-size-fits-all language. Speak differently to first-time enrollees versus returning employees, remote vs. on-site workers, and hourly vs. salaried staff. Include real-life examples and scenarios, and use language that reflects employees' day-to-day reality.

• Repurpose benefits content into short videos, PDFs, or Slack messages
• Host a live (or recorded) Q&A session for employees and their families
• Include visuals and plain language in your communications—remove insurance jargon
• Provide side-by-side plan comparisons that highlight key differences
• Use real-life scenarios to show how different plans work in practice
• Add out-of-pocket cost estimators to show annual financial impact
• Flag new or underutilized benefits (like EAPs, financial wellness tools, or telehealth)
• Post updates in employee portals and common areas for visibility

3. Empower Managers to Be Messengers

Managers are often the first point of contact when employees have questions. But many don’t have the tools to explain benefits or guide their teams. So they may unintentionally create confusion or default to “talk to HR,” which increases your team’s workload during an already demanding season. 

To avoid these issues, start manager training and enablement 4–6 weeks before open enrollment. Emphasize their role in fostering a culture of trust and proactive benefits use, and provide them with simple tools.

• Share talking points, FAQs, and email templates managers can use with their teams
• Encourage them to open team meetings with quick benefit reminders
• Provide guidance on how to spot confusion or misinformation and escalate when needed
• Train them to listen for common concerns, especially from first-time enrollees

4. Prepare Systems and Support Teams for a Smooth Launch

For a strong open enrollment experience, your enrollment platform must work seamlessly across all devices, data must flow correctly to payroll and HRIS systems, and your internal teams must be ready to provide timely support. 

Begin your operational readiness assessment 4–2 weeks before enrollment opens. This is the time to confirm system performance, train internal staff, and establish escalation paths for questions or tech issues.

• Test your enrollment system across desktop and mobile and verify data accuracy between the benefits platform, payroll, and HRIS
• Confirm that plan selections display correctly for different employee types
• Train HR and internal support teams to handle inquiries, troubleshoot access issues, and escalate problems as needed
• Prepare a contingency plan for system outages, high inquiry volumes, or late plan changes
• Ensure employees know where to go for help—create a dedicated contact, helpdesk, or support hub

Consider adopting an AI-powered solution to help employees make smarter, safer decisions when navigating their benefits. With AI, employers can match employees with the right physician for a procedure, guide them toward the highest-quality, most cost-effective care, and recommend benefit plans aligned with their unique needs to avoid “open enrollment remorse.”

5. Track Questions and Feedback in Real Time

Once open enrollment begins, employees will reach out with questions, feedback, or confusion, and HR needs visibility into what’s working and what needs immediate clarification. Consider adopting HR solutions that allow for real-time tracking to help HR fine-tune the process while it’s happening and ensure employees don’t feel lost or ignored.

• Create a shared doc or form to log employee questions and adapt communications on the go, for example, updating FAQs or creating a quick video to clarify
• Track repeat issues and respond with mid-cycle communication updates
• Monitor system metrics (logins, time-on-platform, completion rates) to spot drop-off points, and track who hasn’t responded and follow up
• Use anonymous survey tools to gauge confidence and understanding
• Use final Q&A sessions as both education and insight-gathering opportunities

6. Follow Up and Evaluate After Open Enrollment

The end of the enrollment window is just the beginning of finalizing data, resolving issues, and reviewing performance. It is also an opportunity to reflect on what went well and where you can improve next year’s process.

• Review all enrollment forms for missing or incorrect information
• Submit finalized elections to carriers and follow up on ID card delivery
• Audit payroll deductions and ensure alignment across systems
• Answer outstanding employee questions and confirm elections
• Verify compliance with ACA and healthcare regulations
• Debrief internally and document lessons learned
• Report key insights—like participation rates and cost impact—to leadership
• Collect employee feedback to improve communication and plan design next year
• Consider off-cycle enrollment for voluntary benefits or wellness programs

Wrapping Up

• Open enrollment is more than a compliance task. It’s a moment to build trust, drive engagement, and support your people’s well-being.
• Rising costs and growing employee expectations make preparation and clarity more important than ever.
• A successful enrollment starts early, aligns with employee needs, and uses multiple channels to communicate clearly.
• HR teams should prepare systems, support managers, and track engagement in real time to reduce confusion and errors.
• Post-enrollment follow-up ensures accuracy and gives you the insights to improve next year’s process.

Open Enrollment Checklist for Business Leaders

Open enrollment can be complex, but it doesn’t have to be! VensureHR created an Open Enrollment Checklist for Business Leaders to simplify the process, helping you lead your organization through benefits season with clarity and confidence.

Whether you’re reviewing plan options, communicating with employees, or coordinating with other leaders, this checklist helps ensure nothing falls through the cracks.

What You’ll Get:

• A step-by-step guide tailored for business leaders
• Timeline of key activities to keep you on track
• Tips for communicating changes to your team
• Action items to streamline decision-making

Why It Matters

Open enrollment impacts your people, your budget, and your business. With this checklist, you’ll be equipped to make informed decisions and support your workforce effectively.

Get the Checklist

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