HR’s Trend Report: Enrollment Insights from 18 Million Employees
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By Don King
on January 14, 2026
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Top insights for HR and brokers from 2026 annual enrollment
Welcome to the 2026 plan year. How was annual enrollment—quiet, insightful, or the kind of “character-building” you’d rather not repeat?
Enrollment is one of the best stress tests for your benefits program and the tech behind it.
It’s when employees vote with their clicks: what they understand, what they ignore, where they get stuck, and what they wish you offered.
And when you zoom out across 18 million employees’ experiences captured across our technology, a few patterns show up loud and clear.
Below are the biggest enrollment insights we’re taking into 2026—plus practical next steps you can actually use. No fluff, no “leverage synergies.” Just facts.
Employees want more benefits choice—but is literacy getting in the way?
More employees are asking for broader, more personalized benefits. The problem: many don’t feel confident enough to make decisions when options multiply.
Our data consistently shows benefits literacy is low—86% of employees say they’re confused. And honestly, that’s not a judgment on employees. Benefits are complex. People have jobs. They shouldn’t need an insurance minor to choose coverage.
What Gen Z and Millennials want most:
Gen Z and Millennials make up the majority of today’s workforce, and their “good benefits” definition keeps expanding—especially where life, money, and flexibility intersect. The top benefits they say improve satisfaction and performance at work include:
Financial matching, like 401(k)
Parent and caregiver support
Flexibility and time-off policies
Key insights from annual enrollment:
Only a third of all employees know what accident insurance or an HSA is used for
Less than half understand FSAs and hospital indemnity
What you should do about it:
Pressure-test your benefits materials. Do they translate value in plain language (what it is, when you’d use it, how it helps), or do they read like a plan document in disguise?
Audit your program mix. Is your lineup competitive and diverse enough for different life stages and needs?
Use enrollment signals to guide improvements. Look at enrollment/decline patterns, call drivers, and “where people drop off” in the experience. Confusion leaves footprints.
Let’s be real: most employees aren’t going to dig through a benefits PDF to answer a question they need solved in 90 seconds.
Employees across generations prefer digital-first environments that give them choice in how, when, and where they engage—especially when they’re making high-stakes decisions. That means:
24/7 support when questions pop up after hours
Mobile access that makes benefits usable beyond a desktop
Intuitive design that feels familiar (because nobody wants to “learn” enrollment software)
Key enrollment insights
45% of employees opt in to text message reminders
36% log in 4+ times after enrollment—and that jumps to 42% when communications are in play
18% lift in benefits utilization when the experience is tailored to the user
What to do about it
Build an omnichannel communication strategy. People need repeated exposure to remember—so plan for coordinated touches across email, text, print, and manager toolkits (yes, even break room posters still work).
Get more mileage from your vendor partners. Your voluntary and point solution partners often have ready-to-use communications and engagement playbooks. Ask what’s worked, borrow what’s proven, and adapt it to your population.
Design for “after enrollment.” If employees are logging in multiple times post-AE, meet them there with confirmation messages, easy next steps, and bite-sized “how to use your benefits” nudges.
If there’s one constant in employee sentiment, it’s this: financial uncertainty makes healthcare decisions harder, not easier.
Key enrollment insights
45% of employees say they feel panicked at the thought of an unexpected medical bill
34% say they would go into debt or don’t know how they’d cover an unexpected expense
What to do about it
Make cost clarity a first-class feature. Employees want predictable costs. Bring plan comparisons to life with real examples (common scenarios, paycheck impact, deductible timing).
Position accounts as tools, not acronyms. HSAs/FSAs aren’t “nice-to-haves” if people understand how they reduce out-of-pocket pain. Translate them into simple outcomes: save on taxes, plan for the expected, protect against the unexpected.
Lean into voluntary benefits where they fit. Accident, hospital indemnity, critical illness—these are easier decisions when framed around “what would this protect me from?” not product descriptions.
Target the moment, not the calendar. Use life events, claims triggers (where appropriate), and post-enrollment reminders to drive smarter utilization—not just enrollment volume.
What this means for your 2026 benefits strategy
Annual enrollment isn’t just an admin milestone—it’s a real-time read on what employees need, what they understand, and what’s not working.
If you take nothing else into 2026, take this:
More choice requires more guidance (not more content).
