Each year, Open Enrollment marks a critical moment for millions of Americans to secure, renew, or update their health coverage. For companies that rely on 1099 or flexible workers, it’s also one of the most important windows to demonstrate care and reinforce financial security across your workforce.

In just one year, portable benefits have gone from concept to real impact, helping independent workers save for health, emergencies, and retirement. See how far the movement has come.

Portable benefits aren’t just for drivers. Learn how musicians, nurses, freelancers, and other workers can benefit from flexible benefit models.

On April 10, 2025, Alabama Governor Kay Ivey signed a groundbreaking law making Alabama the first state to offer tax-deductible portable benefits contributions for independent workers.

Stride has been selected by Uber and Lyft to administer health insurance stipends to eligible drivers across the state of Massachusetts.

On April 3, 2025, Governor Bill Lee signed the “Voluntary Portable Benefit Plan Act” into law, making Tennessee the second state in the country to formally enable portable benefits for independent workers.

The Modern Worker Security Act allows companies to support independent workers without reclassification risks. Learn how businesses can prepare for this shift and what it means for workforce strategy, compliance, and talent retention.

Discover how portable benefits are transforming workforce retention in 2025. Learn why companies engaging independent contractors and non-benefited W2 employees are turning to portable benefits programs for sustainable growth.