The Top 4 Contractor Management Trends Shaping 2026
What Economic Upheaval, AI, and Changing Regulations Mean for Your 1099 Workforce
Wingspan Contributors
Greg @ Wingspan
Articles credited to Greg @ Wingspan as author, editor, or reviewer. Each article identifies the contributor’s role.
Articles and contributions
Don’t Make Contractors an Afterthought
How to Build an HR Platform for a Mixed Workforce
Introducing Wingspan Embed: Power Contractor Management Directly Within Your Platform
Legacy HR Systems Weren’t Built for the Modern Workforce
Wingspan vs. Stripe Connect: contractor payments compared
Compare Wingspan and Stripe Connect for contractor onboarding, payments, tax reporting, support, and the work your team will own.
How AI Makes the Future of Work Bursty
As AI drives down the cost of routine execution, flexible work is shifting toward specialized, project-based work that arrives in bursts of creation, then slower stretches of implementation.
Why We Launched Employee Payroll
W-2 payroll and 1099 contractor management, together in Wingspan.
What 500+ HR and Finance Leaders Revealed About Managing Contractors
A contractor management crisis is hiding in plain sight.