Open Enrollment is almost here. You’ve spent months planning, coordinating, and communicating—and now the big day is just around the corner. It’s the HR equivalent of hosting a wedding or putting on a live concert. You’ve built the guest list, hired the band, and set the stage. Now, the question is: will everything run smoothly when the lights come on? 

The good news? With the right final prep, it will. The last few days before OE launch are your chance to test, align, and double-check so that your team feels confident and your employees get the seamless experience they deserve. 

Here are five essential steps to make sure your Open Enrollment kickoff is a success. 

1. Test Before You “Go Live” 

Think of your enrollment platform as the stage. You wouldn’t open the curtain without a dress rehearsal, and you shouldn’t launch OE without one either. 

Run a full system dry run to make sure: 

• Logins work for every employee type. 
• Plan selections flow correctly. 
• Confirmation emails or screens display as expected. 
• Eligibility, plan details, and deduction amounts are accurate. 

Catching a glitch now is infinitely less stressful than troubleshooting on launch day. A little rehearsal goes a long way toward a smoother performance. 

2. Send Final Reminders That Actually Get Read 

Employees are busy, and OE isn’t exactly at the top of their to-do lists. That’s why your final reminders need to be clear, concise, and impossible to ignore. 

A few tips: 

• Use multiple channels—email, SMS, intranet posts—to make sure the message lands. 
• Keep it short and action-focused: “Enrollment closes Friday. Don’t miss your chance to choose.” 
• Share FAQs, short explainer videos, or quick guides to reduce confusion. 

We asked employees about how they want to hear about their benefits, and here’s why it matters: 

• While 74% of employees say they read benefits emails, only 51% say they’ll act when the message feels personal to their situation.
• Nearly 1 in 3 employees admitted ignoring open enrollment messages because they didn’t feel relevant. 
• When communication misses the mark, the impact is real: 39% of employees delayed or skipped care last year because they weren’t sure what their plan covered. 

Think of these reminders as friendly nudges, not nagging emails. The goal is to reassure employees, reduce confusion, and keep everyone on track for a stress-free OE launch. 

Get the Insight to Employee Benefits

Don’t just assume you understand what your employees need, want or prioritize. Check out what the survey says and see how your benefits strategy fits.

3. Align Your Internal Dream Team 

On launch day, your HR and benefits staff are the pit crew in a high-speed race. Everyone has a role, and a fast response to issues keeps everything running smoothly. 

Make sure to: 

• Hold a quick pre-launch huddle to confirm roles and responsibilities. 
• Share a contact list for troubleshooting so employees know who to reach. 
• Give team members a refresher on the enrollment platform and common FAQs. 

When your team is aligned and ready, you can solve problems quickly—and maybe even prevent them from happening in the first place. 

See how HR Teams prepare for Open Enrollment Success

4. Check the Data, Twice (Santa Style) 

Data accuracy is the unsung hero of a successful OE launch. Nothing erodes employee trust faster than logging in to see the wrong premium or ineligible plan. 

Before day one, double-check: 

• Employee eligibility records. 
• Plan details, rates, and deductions. 
• Data synchronization across HRIS, payroll, and benefits platforms. 

Think of it as making your list and checking it twice. Employees will thank you for a smooth, accurate experience. 

5. Monitor Day One Like a Pro 

Even the best-prepped teams need a command center on launch day. It doesn’t have to be fancy—even a shared Zoom room or group chat can work—but having one place to monitor issues in real time makes all the difference. 

Here’s how to set it up: 

• Assign dedicated staffers to complete a test enrollment as if they were employees. 
• Keep vendor contacts on standby for any tech hiccups. 
• Create escalation protocols so no issue lingers too long. 

Think of this as your OE air traffic control tower. When you’re monitoring from above, you can spot problems early and keep everything landing safely. 

Celebrate the Launch (and Your Team) 

Once the first day of OE wraps up, don’t forget to celebrate. Recognize your HR team’s hard work—it takes a lot to pull off a seamless launch. Whether it’s a coffee toast in the break room or a well-earned happy hour, acknowledging the effort boosts morale and keeps everyone motivated for the weeks ahead. 

Ready for the Full Playbook? 

This blog covers the highlights, but the Open Enrollment Kick-Off Prep Checklist gives you the step-by-step framework to finalize every detail before day one. From system testing to communication reminders, it’s everything you need to launch OE with confidence. 

Get the Checklist

Because when it comes to OE, last-minute surprises aren’t part of the plan.