The 2025 Open Enrollment Checklist for HR Teams Who Don’t Have Time for Nonsense

Published on 5/1/24 · Updated 7/9/25

Open enrollment hits differently in 2025. With tighter budgets, virtual teams, and a more skeptical workforce, HR leaders need a smarter way to engage employees and get results. This open enrollment checklist for employers breaks down the must-have tools, strategies, and tech to run a smooth, effective—and dare we say—modern enrollment season.

Whether you’re navigating new plans, managing a hybrid workforce, or looking for the right benefits enrollment tool, this guide will help you cut through the chaos and deliver a virtual open enrollment experience that actually works.

1. Use AI to draft (and personalize) your OE comms

Let AI write the first draft—so you’re not staring at a blank page. Use tools like ChatGPT to build a base, then layer in your tone, empathy, and plan details. It’s faster, and still totally human.

Do this:

• Create segmented email templates (HDHP users, caregivers, etc.)
• Use AI to draft Slack, intranet, and text message reminders
• Run your content through AI to simplify language and improve clarity

Looking for support? Jellyvision’s Custom Solutions team can help you craft high-performing, benefits-savvy comms from day one.

2. Put Ask ALEX front and center

Your inbox doesn’t need to be full of “What’s an HSA?” and “Will this cover my kid’s braces?” Ask ALEX, our AI-powered benefits chatbot, handles routine questions 24/7—with answers grounded in your company’s actual plan documents.

Do this:

• Add Ask ALEX to your intranet or HR portal
• Promote it early with sample questions to try
• Track employee usage to improve FAQs and future messaging

Ask ALEX is part of a complete benefits decision support experience that helps employees feel informed, not overwhelmed.

3. Rethink your webinar—and make it bingeable

Nobody wants a 60-minute Zoom with 50 slides. Instead, deliver your open enrollment webinar like a streaming playlist—short, snappy, and watchable on demand.

Do this:

• Break your webinar into short chapters (2–3 minutes each)
• Add captions and timestamps so employees can skip to what matters
• Embed videos in your emails, intranet, and employee open enrollment materials

4. Create dynamic, not static, benefits guides

Your traditional PDF guide isn’t cutting it. Build an interactive experience that’s easier to navigate and understand.

Do this:

• Use a no-code platform to build an interactive employee benefits guide
• Lead with what’s changed since last year
• Embed short videos or decision support tools like ALEX
• Add a “Need help?” button that connects to Ask ALEX

This transforms your guide from a document into a benefits communication experience.

5. Automate follow-ups with behavioral nudges

Don’t just send reminders—send the right reminders. Use behavior-based targeting to nudge employees who haven’t taken action or might be stuck.

Do this:

• Trigger follow-ups based on engagement data (opens, clicks, logins)
  Target different segments (first-time enrollees, family planners, etc.)
• Reinforce deadlines and resources with countdowns or progress indicators

With tools like ALEX, you can even track where employees drop off—and adjust midstream.

6. Make it mobile-first (or lose them)

Employees aren’t reading your open enrollment materials at their desks—they’re skimming during daycare pickup or while waiting in line at Target.

Do this:

• Optimize all materials (guides, emails, landing pages) for mobile
• Use QR codes to bridge physical and digital spaces
• Include one-tap access to your benefits enrollment tool

Modern benefits communication has to meet employees where they are—on their phones.

7. Turn office hours into insight engines

Open enrollment office hours don’t just offer help—they offer insight. Use them to spot patterns and surface themes your communications may have missed.

Do this:

• Host drop-in Zooms at varied times and time zones
• Track the most common questions and concerns
• Feed those insights back into your open enrollment messaging and tools like ALEX

If you support onboarding and offboarding through ALEX too, you can extend that personal touch year-round.

8. Measure what matters—and adjust in real time

Don’t wait until it’s over to find out what worked. Monitor performance and adjust on the fly.

Do this:

• Track engagement data from ALEX and your HRIS
• Monitor channel performance (Slack, email, intranet)
• Use Ask ALEX queries to refine your FAQs and internal messaging
• Run a post open enrollment survey to capture lessons for next year

Open enrollment should feel like a living campaign—not a set-it-and-forget-it moment.

Open enrollment 2025: Less noise, more impact

2025 open enrollment isn’t about doing more.

It’s about doing what works: clear communication, modern tools, and support that scales.

That’s why ALEX delivers:

• Personalized plan guidance based on real claims data
• AI-powered support with Ask ALEX
• Smarter communication support from Jellyvision’s Custom Solutions team