Originally Published 7/21/21, Updated on 7/8/25.
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.
If you need help with benefits emails year-round, Jellyvision Custom Solutions is the answer!
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
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.
Pro Tip: ALEX can help!
Create a QR code for your benefits engagement tool!
Your team members have used QR codes for the past few years at restaurants and shops—and you should too! Using a QR code on printed materials is an easy way for your employees to access ALEX on the go during open enrollment, and get the benefits information they need when they need it.
Services like QR Code Monkey, QR Code Generator, or Flowcode help you create a QR code that links to your company’s open enrollment software in a matter of minutes. You’ll also be able to brand and track your links, so you know how often they’re being used. Or, if you’re using Google Chrome, you can click the URL bar and a small, square icon will appear to the far right. Click it and a QR code will be generated, ready for you to download!
Your employees can simply scan the QR code with their phone’s camera—and boom! You’ve got folks engaging with your benefits engagement tool in a new, faster way.
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
CTA: Ready to deliver an OE experience your employees will actually trust?
Get a demo
FAQs About Your Open Enrollment Checklist
What should be included in an open enrollment checklist for employers?
A good checklist includes updated guides, email and video communications, a benefits decision support tool, AI-powered chat, and follow-up strategies based on employee behavior.
What is the best way to communicate benefits changes?
Use simple, segmented messaging. Short videos, visuals, and smart tools like ALEX help cut through the noise.
How can HR teams use AI during open enrollment?
AI can help write content, personalize communications, power chatbots like Ask ALEX, and surface real-time insights from employee behavior.
What are the top virtual open enrollment tools for 2025?
Tools that combine plan education, live support, and real-time tracking—like ALEX—are leading the way.
Should I still use a printed benefits guide?
It depends on your audience. But pairing a short print piece with a mobile-friendly, interactive guide offers the best of both worlds.
How do I improve employee engagement during OE?
Keep it short, mobile-accessible, and personalized. Track what’s working—and adjust quickly.
Where can I learn more about ALEX?
You can start with a quick ALEX demo to see how it works.
