Is Your Enrollment Experience a 10/10? If Not, Here's What You're Missing
- choutz
- Jun 2
- 3 min read
Let’s Talk: How’s Your Enrollment Season Really Going?
Be honest—does it feel smooth, thoughtful, and supportive? Or more like a frantic scramble between the jobsite, paperwork, and late-night calls from confused team members?
If you're not rating your open enrollment a 10 out of 10, you're not alone. But here's the thing—you don’t have to settle.
Why Enrollment Season Feels Like a Headache (And Doesn’t Have To)
If you're running a blue-collar business—whether it’s a plumbing outfit, a concrete crew, an HVAC company, or a family-run mechanic shop—chances are you’re juggling a hundred things every day. Insurance is probably not the first thing you want to deal with, especially during open enrollment.
Maybe you just renew last year’s plan without thinking much about it. Maybe your crew has no idea what their coverage really includes. Or maybe you’ve tried to offer benefits, but it feels like the options are too expensive or too confusing.
Here’s the truth: A lot of small businesses with 2 to 75 employees feel this way. And yet, every year, they go through the same rushed, overwhelming experience—not because it’s the best way, but because they didn’t know there were better options.
Many business owners don’t realize that the insurance market has shifted. There’s been a major push toward modern, tech-enabled enrollment experiences, even for small groups. Carriers and brokers are starting to invest in tools that simplify the renewal process—platforms where employees can compare plans, enroll via their phones, and even access benefit education videos tailored to their needs.
Let’s Imagine a Different Kind of Enrollment
Picture this: You know exactly when enrollment starts and ends. Your broker reaches out early to walk you through your options. Your crew? They’re not just handed a packet and left to figure it out—they actually understand what they’re signing up for. Someone even takes the time to explain the differences between plans, coverage details, and what it means for their families.
Better yet, your benefits package isn’t just about checking a box. It’s designed to fit the way your team works and lives. Maybe that means adding affordable accident insurance or short-term disability. Maybe it means switching to a platform that works on mobile phones, so your guys can enroll between jobs.
And that broker? They’re not just a name on an email. They’re your partner—checking in, solving problems, and making sure nothing falls through the cracks.
This isn’t a fantasy. This is what a 10/10 enrollment experience actually looks like for businesses like yours.
What If There’s a Better Way—Wouldn’t You Want to Know?
It’s easy to assume that better service, better plans, or smarter tools are only for the “big guys.” But you don’t need 200 employees or a dedicated HR team to have a great enrollment season.
There are solutions tailored to small, blue-collar shops like yours—benefits that fit your team’s needs and your business’s budget. There are supplemental coverages that close the gaps without breaking the bank. There are enrollment strategies that actually work, without overwhelming your people.
And in 2025, more carriers are leaning into digital-first strategies—automated renewals, cleaner plan comparison tools, and streamlined ID card delivery. These things may sound like small upgrades, but for a team that works on rooftops, in basements, or behind the wheel, they make all the difference.
You just need the right guide.
Let’s Make This Your Best Enrollment Season Yet
If enrollment has felt like a rushed chore in the past, let’s change that. It doesn’t have to be a mess of paperwork and unanswered questions. It can be organized, clear, and—dare we say—simple.
Whether you're reviewing benefits for the first time in years or just want to make sure you're not missing anything, we’re here to help.
Free PDF Downloadable Checklist
💬 Let’s talk. We’ll take a look at your current setup, answer your questions, and show you what other businesses like yours are doing.
Comments