Open Enrollment: The Love-Hate Season HR Knows All Too Well
- FitPros Workplace Wellbeing
- May 27
- 4 min read
Updated: May 27
OE: That magical time of year when HR professionals both look forward to it and can’t wait for it to be over.

Written by Lindsay Johnson, FitPros CEO & Founder
Employees rely on the benefits you offer to stay healthy, plan families, tackle life’s curveballs, and save for the future. But while you’re laser-focused on delivering top-tier offerings, somehow you're also expected to become a master event planner, comms guru, and engagement wizard.
But wow... can we talk about the mountain of work it takes to get there?
After months of wrangling carrier contracts, renewal rates, and legal approvals, you're rewarded with… low attendance at your OE meetings and glazed-over stares while reps explain plan changes in monotone. No shade to our well-meaning carrier partners—but let’s be honest: they’re not exactly lighting up the stage.
And despite all that effort? Employee engagement during OE still often falls flat.
Need proof? Here’s what the data says:
💤 Only 28% of employees say they fully understand the benefits their employer offers.
📉 Nearly 40% of employees don’t review all their benefit options during OE.
📱 More than 70% of workers say they'd prefer personalized, interactive benefits education over traditional formats.
📊 56% of HR leaders say employee engagement during OE is their biggest challenge.
🎯 Organizations with higher OE engagement report better year-round benefits utilization and increased employee retention.
That’s where FitPros comes in.
For nearly ten years, FitPros has helped companies transform the traditional Open Enrollment experience. Our Onsite and Virtual Health Fairs deliver important benefits info without the snooze factor. We engage employees with energy, real-life context, and a human-first approach that brings OE to life.
Check out our promo video here to see for yourself!
Here’s a quick breakdown of our Health Fair offerings:
🎉 Full Onsite Health Fair
The full OE experience with high energy and high touch is ideal for groups with 150 employees or more.
Up to 15 vendor tables, including carriers and local wellness vendors
A live DJ, chair massage, and snack station to energize the vibe
Branded tote bags, a Wellbeing Passport Challenge, and raffle prizes to drive participation
3 onsite FitPros staff + a Success Manager
Certificate of Insurance collection handled by us
Engagement app for seamless employee access and communication
🎈 Mini Onsite Health Fair
A scaled-back version of the Full Fair—big impact, smaller footprint for groups sized 50 to 150 employees.
10 vendor tables, including key benefits partners and local wellness pros
Includes a chair massage, snack station, raffle prizes, and branded tote bags
1 onsite FitPros staff member + Success Manager
Wellbeing Passport Challenge* to gamify the experience
Engagement app for easy scheduling, updates, and social buzz
🌱 Lite Onsite Health Fair
Ideal for smaller teams of 50 or less. Simple, fun, and impactful.
Focused format with benefit carriers, a nutritionist, and a local gym or yoga partner
Includes a chair massage, snack station, raffle prizes, and Carrier Passport Challenge
Dedicated Virtual Success Manager and COI collection
Same robust engagement app for employee participation and promotion
💻 Virtual Health Fair
A fully digital, highly interactive experience ideal for remote or hybrid teams. Many companies add a Virtual Fair to the Onsite experience.
Up to 6 hours of coordinated benefit sessions led by carriers and wellness pros
Access to a LIVE Content Calendar featuring 80+ virtual sessions across the month
A Team App-Based Challenge to boost engagement
Hundreds of on-demand sessions for flexible learning
Engagement app for easy registration, session reminders, social sharing, and push notifications
Making Open Enrollment Less of a Headache (and More of a Hit)
We get it—HR, People Ops teams, and brokers are under intense pressure during Open Enrollment. You're expected to coordinate complex benefit packages, manage internal comms, and ensure every team member understands what’s available to them—all while handling a hundred other priorities.
FitPros supports your efforts by taking OE engagement off your already overflowing plate. We don’t just facilitate carrier participation—we elevate it with gamified learning, expert panels, and both onsite and online excitement that employees actually want to attend.
Now, a little real talk: these Fairs are a lot of coordination. (We know how carriers can be—wink.) That’s why we ask for eight weeks’ notice to make the magic happen. And your legal team? They’ll typically want two weeks to review our Master Services Agreement. It’s a simple doc—but legal’s gonna legal.
Ready to make OE less chaotic and more meaningful?
👉 Talk to us here to learn about this month’s special offer with your Fair purchase.
Let’s transform Open Enrollment from “Ugh, here we go again” to “Wow, that was actually fun.”
Looking for more? Contact a Wellbeing Manager to discuss your organization's wellbeing needs.

We provide workplace teams with mindful practices, personal and professional wellbeing growth, fitness instruction, and opportunities for social connection. We aim to inspire the highest potential in people at work, in life, every day, so they can show up healthy and at their best.