Open Enrollment: What Every Company With 1099 Workers Should Know
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.
With Open Enrollment kicking off on November 1 and running through January 15, we’ve compiled the changes companies should be aware of this year and how your organization can take action to help your workers stay covered and protected.
Why Open Enrollment Matters for Companies with 1099 Workers
For independent contractors and flexible workers, Open Enrollment is often the only chance to get affordable health coverage. When workers miss that window, they can face a year without coverage and costly gaps that affect their ability to work and stay financially secure.
By supporting your 1099 workforce during this period, your company can:
Reduce financial stress that can impact worker engagement
Strengthen retention and loyalty among your top performers
Build your reputation as a worker-centric organization
Portable benefits like health coverage access aren’t just a perk; they’re a source of financial security for workers and a brand differentiator for companies.
What’s Changing for Open Enrollment for 2026 coverage
This year’s enrollment cycle brings a few notable updates that companies should understand:
Premiums and subsidies look different.
Marketplace premiums are expected to rise in many states, but most workers will continue to qualify for significant federal subsidies that keep coverage affordable. Plan options may shift, so reshopping is essential to avoid surprise price changes.
Marketplace verification is getting stricter.
More workers will need to provide additional documentation to confirm income, residency, or immigration status. That means guidance and reminders from companies (and from Stride) are more important than ever to prevent coverage delays or denials.
Auto-renewals aren’t guaranteed.
Many marketplace plans will not automatically renew this year. Workers who don’t actively review their plans could lose coverage or face unexpected cost increases in January.
Federal outreach may be limited.
With reduced federal marketing budgets and fewer CMS awareness campaigns, private companies play an even bigger role in spreading the word. That means your company’s emails, in-app notifications, and worker communications are crucial for ensuring engagement.
What This Means for Workers — and How to Support Them
Most workers don’t realize how easy it is to miss out on savings or lose coverage during Open Enrollment. The best thing they can do is act early, ideally before December 15 (the deadline to apply for coverage starting January 1).
Encourage your workers to:
Reshop and compare plans to ensure they’re still getting the best value.
Submit verification documents promptly to avoid delays.
Ask questions if they’re unsure. Stride’s Member Experience team is here to help!
Act early to prevent coverage gaps and provide peace of mind heading into the new year.
Stride is here to help independent workers, and the companies that support them, navigate Open Enrollment with confidence. Our platform helps users choose plans, confirm subsidies, and avoid coverage gaps.
Ready to support your workers this Open Enrollment?
Connect with your Stride Partner Manager, or reach out to our team to learn more about how Stride can support your workforce during Open Enrollment and year-round.