Tax Day 2025: Important 1099 Tax Deadlines
If you're an independent worker, you can expect to receive your 1099 form when tax deadlines are approaching. Don't worry, we've rounded up all the important dates you need to know about so you don’t miss any.
Stride and Roadie Partner to Empower Drivers with Financial Tools
We’re teaming up with Roadie, a UPS Company and a logistics management and crowdsourced delivery platform, to provide comprehensive support to independent drivers nationwide.
Getting Health Insurance Throughout the Year
If you experience a “Qualifying Life Event," you may be eligible to enroll for health insurance during Special Enrollment Period. Read on to see if you qualify.
I Missed Open Enrollment for Health Insurance, Now What?
Did you miss health insurance Open Enrollment? Learn your options and next steps in our guide.
Stride Launches Utah's First Independent Worker Portable Benefits Contributions Program
On the heels of last week’s exciting announcement, w’re launching the Stride Contributions program in Utah, following the state’s passage of new Portable Benefit Plan legislation (SB-233), which creates opportunities for companies to extend more benefits to 1099 workers.
Introducing Stride Save* with Contributions: The Future of Worker Benefits
Today, we’re thrilled to announce that we’re expanding our portable benefits suite with a first-of-its-kind innovation, Stride Save, to help independent workers set aside money for savings and essential benefits.
What Is Supplemental Insurance?
What is supplemental insurance? Check out our comprehensive guide and learn about the types, benefits, and how to get extra coverage.
Taxes 101: Common Tax Terms You Need To Know
As an independent contractor, taxes can be complicated. Here's a guide to understanding tax terms, plus resources for 1099 workers to make taxes simple.