About Benrollment

Redefining the Benefits Gap

Your Partner in Portable Benefits.

Benrollment was created to close the benefits gap for the 60–70 million Americans who work outside the W-2 model. We connect independent workers with health, dental, vision, disability, life, and supplemental insurance options that travel with them from gig to gig, contract to contract, and city to city. Powered by The Meehan Agency, our platform blends decades of enrollment expertise with modern technology so independent workers can finally compare and enroll with clarity.

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Let's get you covered

The Basics You Need to Know.

Every business has a story, and ours begins with a simple goal—making benefits easier for people who work outside the traditional system. Here’s a quick look at who we serve, what we do, when and why we started, and how we help workers across the country today.

Who Do We Serve?

Whether you are self-employed, a 1099 contractor, a gig worker, a retiree or an individual in need of a specific type of coverage for yourself or your family, the Benrollment program is designed to get you direct access to the coverages that you need.

What Do We Do?

Benrollment is an online marketplace that brings together multiple carriers, side-by-side plan comparisons, and flexible enrollment options—online self-service or counselor-assisted.

When Should I Apply?

We were built to meet today’s workforce realities. Independent work is growing fast, and millions of people need portable benefits right now—not just during Open Enrollment.

Where Can I Get Started?

Our services are available nationwide, but every plan is issued under your state of residence and must meet state Department of Insurance requirements. Availability varies by state, and Benrollment helps you navigate what applies where you live and work.

Why Should I Enroll?

Because independent workers (1099, contractors, self-employed, sole proprietors, small employers, etc.) deserve the same security and choice as traditional W-2 employees. Benrollment exists to give freelancers, contractors, and gig workers a single place to compare options, understand coverage in plain English, and enroll confidently.

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Frequently asked Questions

Your Top Questions, Answered

Independent workers often have similar concerns when exploring benefits. Here are a few of the most common questions, with clear, simple answers.

  • Do self-employed people qualify for health insurance?

    Yes. Self-employed individuals and 1099 contractors can buy health insurance through the ACA marketplace, private carriers, or platforms like Benrollment that let you compare multiple options in one place.

  • Can I enroll outside of Open Enrollment?

    For medical coverage, you typically need to wait for Open Enrollment or qualify for a Special Enrollment Period (like a move, new child, or loss of coverage). Supplemental plans—like dental, vision, accident, or disability—are often available year-round.

  • Are benefits the same in every state?

    No. Each state regulates insurance differently. Plans are issued based on your state of residence, and availability varies. Benrollment makes it clear which options apply where you live.

  • Do I need a benefits counselor to enroll?

    Not at all. You can self-enroll online anytime. But if you’d like help comparing plans, a licensed benefits counselor can walk you through your options at no extra cost.