The Open Enrollment Launch Checklist: Things Not to Forget in the Final Two Weeks

Open enrollment is approaching fast. The strategic planning is behind you, the communications calendar is set and your goals are defined. Now it's about the execution of focused, deliberate work that turns a well-laid plan into a clean go-live. 

The final stretch of open enrollment can feel overwhelming. HR leaders are often juggling system testing, last-minute communications, manager enablement and support staffing all at once, with little clarity on what "ready" actually looks like. That's why we've put together a week-by-week open enrollment launch checklist of things to be aware of as you head into your final two weeks. 

Two Weeks Out: Confirm Your Foundation 

Two weeks before go-live is your opportunity to make sure the foundation is solid. This is the window to test, verify and align before the pressure of enrollment traffic arrives. 

• Finalize enrollment platform testing — Complete a full quality assurance (QA) pass of the enrollment portal. This could include reviewing data loads, plan configurations, carrier file setup and end-to-end login flows. Document any issues that need to be resolved by your benefits administration provider. 
• Verify plan details — Confirm all plan rates, carriers and benefit offerings are loaded and accurate. A single incorrect rate can create confusion and impact employee trust. 
• Lock the communications schedule — Finalize the dates for your kickoff, reminders, and deadline pushes so your team and your employees know exactly what's coming and when. 
• Check in with stakeholders — Confirm readiness with IT, carriers and HR operations. Make sure key dates are locked and everyone understands their role in the launch. 
• Confirm decision support and enrollment tools are live and tested — Verify that plan comparison tools, decision support and enrollment resources are accessible and functioning on the benefits portal so open enrollment is as smooth as possible for your employees. 

One Week Out: Enable Your People and Support Channels 

With one week to go, the focus shifts to the people side of the launch. This is where you set up the support systems that will carry your employees through their enrollment decisions and give your managers the tools they need to guide them. 

• Prepare your managers — Distribute manager talking points, FAQs and a short briefing so frontline leaders can answer employee questions with confidence. Managers are often the first person an employee turns to with a benefits question. 
• Verify support channels —Test your employee support channels before questions start arriving, such as a dedicated open enrollment email inbox or employee benefits contact center. Being proactive means your employees can get help when they need it. 
• Confirm availability of employee resources — Make sure links to decision support, plan comparison tools and FAQs are easy to find and functional on the benefits portal. 
• Finalize and document contingency plan — Assign on-call owners for go-live issues, like portal downtime, incorrect rates and call volume spikes. Document the escalation paths so everyone knows who to contact and when. 
• Send the one-week reminder — This is your first high-urgency employee touchpoint of the final stretch. A clear, direct message with a link to the enrollment portal keeps momentum building. 

48 Hours Out: Final Readiness Check 

Two days before launch is an optimal time for a final readiness check. This is your go/no-go moment and the final opportunity to catch issues before your employees do. 

• Deliver final reminder — Send the 48-hour countdown message to all eligible employees with a direct link to enroll. This has the potential to be the message that drives the most last-minute participation. 
• Complete a portal stress test — Confirm the enrollment platform can handle expected traffic and that logins work end-to-end. A smooth technical experience can be much appreciated by your employees during what can be a stressful season. 
• Perform a go/no-go review — Hold a series of quick standups with HR Ops, IT, carriers and your benefits administration provider to confirm everyone is ready and no blockers remain. 
• Brief support staff — Make sure hotline and email teams have the current FAQs, plan details and escalation contacts they need to help employees quickly. 
• Prepare launch-day monitoring — Confirm who's watching portal performance, enrollment volume and issue logs in the first 24–48 hours. 

Launch Day: Go Live and Monitor 

Launch day is here. The planning, testing and alignment all come together in this moment and the first few hours set the tone for the entire enrollment period. 

• Send the launch-day announcement — A clear, direct message with the enrollment link and support options. Make it easy for employees to take action immediately. 
• Monitor portal performance — Watch login and enrollment volume through the first hours. Early data tells you whether your launch is running smoothly or needs attention. 
• Triage issues against the contingency plan — Escalate blockers immediately and log minor issues for post-OE review. Having a plan means you can respond quickly and keep employees moving. 
• Check support channel volume — Adjust staffing if call or email volume is higher than expected. Your employees deserve responsive support when they're making important decisions. 
• Capture early signals — Note any recurring employee questions or points of confusion so you can address them in your mid-cycle communications.

You've Launched — Here's Your Next Step 

A successful open enrollment launch is the result of the small, deliberate steps you take in the final two weeks. By confirming your systems, enabling your people and planning for the unexpected, you've set the stage for a smooth enrollment experience for your employees and their families. 

Once open enrollment winds down, taking time to review how it went is what helps to turn this year's experience into next year's improvements. Reflecting on your successes and identifying areas for growth helps you continuously support your employees in the moments that matter, during enrollment and beyond. 

For playbooks, an interactive scorecard and 20+ survey questions to help guide your post-enrollment review and plan for an even stronger season next year, download our Benefits Open Enrollment Review Toolkit.