Open enrollment checklist: A step-by-step guide for HR teams

Open enrollment is one of the busiest times of year for HR. While the actual enrollment window is relatively short, the event requires weeks (or months) of strategic planning and careful preparation. 

Within the context of an open enrollment best practice checklist, we’ll break the event into five phases: plan, prepare, launch, monitor, and reconcile. Along the way, we’ll show how the right employee benefits management software can improve data accuracy and the employee experience. That way, you’re set up for your most successful open enrollment yet. 

Note: This checklist focuses on U.S. employer-sponsored benefits. Requirements vary by plan type, workforce, and jurisdiction, so confirm the obligations that apply to your organization with your broker, carrier, plan administrator, or legal counsel. 

Key takeaways

• An open enrollment project plan commonly has five phases: plan, prepare, launch, monitor, and reconcile. 

• As a practical starting point, begin planning 12 or more weeks before the enrollment window, then adjust the schedule for carrier deadlines and organizational complexity. 

• The first four phases primarily focus on updating benefits, configuring the enrollment platform, creating communication materials, training HR and management, and tracking participation. 

• The last phase is about election and deduction accuracy, as well as reflection on lessons learned. 

• Tools like Dayforce can help guide employees toward best-fit benefits while supporting eligibility and compliance-related workflows and reducing administrative work. 

The open enrollment project plan timeline

A sound open enrollment project plan starts with a clear schedule of what needs to happen and when. Follow a timeline like the one below, and you won’t need to scramble to get things done at the last minute. 
 

Phase 1: Plan and design open enrollment

In this sample timeline, planning begins 12 or more weeks before open enrollment. More complex renewals, plan changes, or carrier transitions may require an earlier start. 

The main tasks for this phase: 

• Revisit the key metrics from the previous open enrollment, such as participation rate and support ticket volume, to optimize this year’s event. 

• Review last year’s benefits usage and collect employee feedback to identify potential gaps in your suite of perks. 

• Determine the plan year to anchor your open enrollment timeline. 

• Set your annual benefits budget to guide plan design decisions. 

• Meet with your broker or benefits advisor to discuss plan design changes and the federal, state, carrier, and plan-specific requirements that may apply. 

Pro tip: Check out our ultimate guide to employee benefits administration to get ahead of some common benefits-related challenges. 

Phase 2: Prepare for open enrollment 

While phase one focuses on strategy, phase two focuses on action. Here’s your open enrollment best practice checklist for this leg of the process: 

• Configure your enrollment platform with new benefits, premiums, contribution limits, and eligibility rules. 

• Test the platform extensively before it goes live and fix any bugs 
• Review the notices and disclosures that apply to your plans and workforce, and confirm the required recipients, timing, content, and delivery method. For U.S. group health plans, examples may include: 
  • Summary of Benefits and Coverage (SBC)  
  • Annual CHIP notice, where applicable  
  • WHCRA annual notice  
  • HIPAA special enrollment disclosures  
  • Newborns’ Act information  
  • Medicare Part D creditable coverage notices for Medicare-eligible individuals 

• Confirm that Summaries of Benefits and other enrollment materials accurately reflect final plan terms and are consistent with carrier or third-party administrator documentation. 

• Develop your open enrollment communication plan and materials. 

• Note who is taking ownership of each task and hold them accountable to the open enrollment project plan timeline. 

Keep these guidelines in mind as you create your open enrollment communication plan: 

• Make messages clear, concise, and accessible. 

• Create written, audio, and video materials. 

• Tailor messages to different employee segments, such as parents or those nearing retirement. 

• Broadcast messages from a variety of channels, such as email, text, webinar, and live training. 

• Send several reminders throughout the open enrollment window. 

Phase 3: Launch open enrollment

When you reach phase three, it’s almost time to hit the “go” button. But before you do:  

• Train HR and managers on key dates, approved talking points, and where to route plan-specific, personal, or complex questions. 

• Run a final check on the enrollment platform and switch it from test mode to live. 

• Send an announcement that open enrollment is about to begin and include the deadline to enroll and the link to the platform. 

• Encourage employees to enroll as soon as possible. 

Phase 4: Monitor during the enrollment window

After weeks (or months) of planning and preparation, the big event is here. Here’s what to do to keep it on track: 

• Pull daily reports from the self-service benefits enrollment software on participation by segment. 

• Send frequent enrollment reminders with the deadline prominently displayed (at least one at the midpoint and one towards the end), with an extra focus on segments with low participation. 

• Make it easy for team members to get live enrollment assistance. 

Phase 5: Reconcile after enrollment closes

The enrollment window closing doesn’t signal the end of the season for HR and payroll professionals. Here’s what needs to happen as soon as the deadline has passed: 

• Reconcile elections, coverage waivers, dependent data, and carrier acknowledgements or enrollment files, as applicable. 

• Confirm that benefit elections are mapped to the correct payroll deductions, effective dates, and per-pay-period amounts. 

• Run a test pay calculation and confirm that expected and calculated deductions match. 

• Send each employee a personalized confirmation of their elections and explain how to report suspected errors promptly. Handle corrections and post-enrollment changes according to the plan’s written terms and applicable election-change rules. 

• Complete dependent-verification reviews and follow the plan’s documented process for reminders, review, appeals, deadlines, and any resulting coverage changes. 

• Review open enrollment metrics, such as participation rate, to lay the groundwork for next season’s strategy.  

How the right tools support HR and open enrollment 

The right tool can support many of the items on your open enrollment best practice checklist. For example, effective benefits enrollment software can: 

• Model plan design changes and run “what-if” scenarios before finalizing choices. 

• Apply configured rate tables, contribution limits, and eligibility rules to each employee automatically, reducing manual data entry and tracking. 

• Provide a guided enrollment process and decision support to each employee. 

• Provide reporting that helps administrators monitor enrollment status and participation. 

• Send automatic enrollment reminders to employees who haven’t completed the process. 

• Support carrier exports and surface data issues that administrators need to review. 

While software can improve the open enrollment experience for both your company and your employees, it can’t take all benefits-related tasks off your plate. If you’d rather focus on other initiatives, consider outsourcing benefits administration to a managed benefits services provider. 

Frequently asked questions

What should be on an HR team’s open enrollment checklist? 

Start by reviewing current benefits usage and asking employees for feedback. From there, prepare your required compliance notices and meet with your broker to review plan renewals and discuss any updates to plan design. 

Next comes communication. Build a strategy that reaches employees across channels and formats, tailored to different segments of your workforce, so the right message lands with the right group. At the same time, configure your enrollment platform with updated benefits, premiums, contribution limits, and eligibility rules. 

Once enrollment opens, track participation and stay available to support employees who have questions along the way. When the window closes, confirm that enrollment data is captured accurately and reflected correctly in both payroll and your carrier feeds. 

When should HR teams start preparing for open enrollment?

HR teams ideally start preparing for open enrollment at least three months before employees can enroll. If the company operates in multiple states, you’re switching carriers, you’re dramatically changing your benefits package, or your situation is otherwise complex, consider padding that timeline with an extra four to eight weeks. 

What are the main phases of an open enrollment project plan?

The main phases of an open enrollment project plan are plan, prepare, launch, monitor, and reconcile. The first two lay the groundwork for the event. The third involves final preparation and opening the enrollment window. The fourth focuses on tracking participation and sending reminders. The last deals with ensuring data accuracy and compiling key takeaways. 

How can HR teams reduce common open enrollment mistakes like missed deadlines or data errors? 

HR teams can reduce common open enrollment mistakes by doing things like: 

• Starting the process sooner to avoid feeling rushed 

• Testing the system configuration to avoid enrollment errors 

• Using a compliance calendar, documented workflows, and reminders to help track applicable notice and disclosure deadlines 

• Running audits on enrollment records to avoid having incomplete files 

How does Dayforce support HR teams through the entire open enrollment cycle? 

Dayforce supports key stages of open enrollment through connected benefits and payroll data, configurable eligibility rules, self-service enrollment, guided choices, reporting, reminders, and benefits administration tools. When Dayforce Benefits and Payroll are configured together, benefit elections can flow into payroll deductions, helping reduce duplicate data entry. Dayforce can also present employees with only the options they’re eligible for and provide smart recommendations to support informed choices.