Contractor & Freelancer Coverage Solutions

A 1099 workforce can't join your group health plan the way W-2 employees can, but that doesn't mean you can't help them get covered. Here's how the two paths compare.

1099 support
Stipend options
Boosts retention
Contractor & Freelancer Coverage Solutions
Two Workforces, Two Paths

W-2 Group Benefits vs. 1099 Contractor Support

The right approach depends on how each part of your workforce is classified. Here's how the two paths differ in practice.

W-2 Employees

Eligible for your traditional group health plan. You share premiums directly and everyone enrolls under one policy.

Best fit: staff on payroll, subject to employer withholding.

1099 Contractors

Generally cannot join your group plan without creating misclassification risk. Supported instead through a stipend or guided individual enrollment.

Best fit: independent contractors who invoice for their work.

Ways Businesses Support Contractor Coverage

  • Stipends. A flat monthly amount contractors put toward their own plan. Simple, predictable, and appreciated.
  • Guided enrollment. We work with your contractors individually to find them Marketplace or private coverage, at no cost to your business.
  • Hybrid teams. If you have both W-2 and 1099 workers, we design a group plan for staff and a separate stipend or guided-enrollment approach for contractors.

Why This Matters for Retention

Contractors with stable coverage stick around. Helping them solve health insurance is one of the cheapest loyalty investments a contractor-driven business can make.

Contractor Benefits Questions

Can I put 1099 contractors on my company's group health plan?

Generally no. Group health plans are designed for W-2 employees, and adding contractors can create misclassification risk. Instead, employers typically support contractor coverage through a stipend, guided individual enrollment, or a similar arrangement outside the group plan.

What's the simplest way to help contractors get covered?

A flat monthly stipend that contractors put toward their own individual or Marketplace plan is the simplest approach. It's predictable for your budget and gives contractors flexibility to choose coverage that fits their needs.

How do I handle benefits if I have both W-2 employees and 1099 contractors?

Most hybrid teams run a traditional group plan for W-2 staff and a separate stipend or guided-enrollment approach for contractors. This keeps each group on the coverage path suited to their employment classification.

Have a Mixed W-2 and 1099 Team?

Tell us your workforce mix and we'll help you design the right coverage path for each group.