Open enrollment survival tips
6 ways to help employees understand and use their benefits
By Jeremiah Wiggins, People Operations Manager, Reperio Health
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Open enrollment is the stretch of the year when every benefits question arrives at once.
Employees are comparing plans they only look at once a year, and HR is answering questions while keeping the whole process on schedule.
I've spent nearly a decade building people functions at growing companies, from a multi-site surgery center in Atlanta to health-data company Springbuk. This year I'm running my first open enrollment at Reperio. My background is in psychology, and the lesson I keep coming back to is this one:
“Communicating a benefit and helping someone understand its value are two different things.
Here are six things I'd tell any HR, benefits, or people leader
in the middle of OE.
Put the links within reach before anyone asks
Send one “where everything lives” note the day enrollment opens: HRIS login, carrier portals, plan guide, deadline, who to ask. Make information accessible before it becomes urgent. We can provide employees with every resource imaginable, but if they don't know where to find them when needed, then we've only created another barrier.
“The links you don't need until you do.”
Don't mistake communication for engagement
Employees are balancing their own workloads and priorities, so a benefits email is likely one of a few dozen they receive that day. Think beyond whether a message was delivered and consider whether employees understand what action they need to take.
Test the whole flow before invites go out
Run a test enrollment end to end with your broker, then confirm deductions land correctly in payroll. A seamless enrollment experience requires as much attention to what employees don't see as what they do.
“It's better to have it set up before you actually need it.”
Design for how people decide
Open enrollment often asks employees to navigate unfamiliar terminology, competing plan options, and decisions that could affect their families for an entire year. The goal is to simplify the decision-making process without oversimplifying the decisions themselves. Employees should leave open enrollment feeling confident in their choices and not just relieved that they've completed the process.
Make HR feel human
Create room for the questions employees hesitate to ask. Benefits can be deeply personal, and employees don't always feel comfortable admitting they don't fully understand their options. One thing I try to remain conscious of in HR is that familiarity with a process on our end doesn't mean familiarity on theirs.
Remind people what they already have
A benefit's real impact depends on whether employees know it exists and understand how to access it. Otherwise, even a well-designed benefits package risks becoming an underutilized investment. Open enrollment creates a natural opportunity to remind everyone of resources that are often overlooked or misunderstood.
After the deadline
The enrollment window closes on a set date. Questions about benefits keep coming all year, so the habits that get you through OE are worth keeping long after the deadline passes.
About the author
Jeremiah Wiggins is People Operations Manager at Reperio Health. He builds the people systems that keep growing teams running smoothly, with a psychology lens and nearly a decade in HR across healthcare and tech. Based in Dallas.