Future of Work Why Contractors Are Frustrated With the Companies They Work for (and Why It Matters) It starts with onboarding pain, but it doesn’t end there.
For Contractors Wingspan Product Update: Intl. US Persons Support Not every contractor living abroad should be treated as an international payee.
For Contractors Wingspan Product Update: Work Logging Managing contractor work hours shouldn't require spreadsheets, separate time-tracking tools, or support tickets.
Future of Work Why Independent Contractors Are the Backbone of the Modern Workforce For them, it’s more than a gig.
Payments Scaling the Flexible Workforce: Beyond AP Automation to Revenue Protection Discover how a purpose-built system ensures compliance, speeds up payments, and protects your bottom line.
Future of Work What 500+ HR and Finance Leaders Revealed About Managing Contractors A contractor management crisis is hiding in plain sight.
Updates Q1 2026 Wingspan Product Updates At Wingspan, we’re focused on solving the unique needs of contractors across the entire management lifecycle.
For Contractors Why Location Matters for Freelancers Working In These States Some states are not like the others.
Compliance Best Contractor Payroll Services: A Guide to Paying Freelancers and Staying Compliant (2026 Edition) Why Modern Enterprises are Moving Beyond Manual Payroll
Payments Buyer's Guide: How to Evaluate Contractor Management Platforms in 2026 Move beyond legacy AP tools and discover how modern platforms automate compliance, accelerate onboarding, and unlock the full potential of your contingent workforce.
Future of Work The Top 4 Contractor Management Trends Shaping 2026 What Economic Upheaval, AI, and Changing Regulations Mean for Your 1099 Workforce
For Contractors When Are Estimated Taxes Due in 2026? The next payment is due sooner than you might think.
For Contractors 20 Free Productivity Apps and Tools to Supercharge Your Business Want to streamline your operations, learn new skills, and spark creativity? Start here.
Future of Work Why Contractors Will Be Essential to Your Company in 2026 These highly skilled professionals are the future of the modern workforce.
For Contractors Why Contract Work Is Perfect for This Moment Your next side hustle could start today.
Future of Work The Top Trends of 2025: What We Predicted Correctly (and What Didn’t Come True After All) 4 Experts Predicted These Top Trends for 2025 - How Did They Do?
Compliance 3 Experts on Managing 1099 Behavioral Health Networks How to Build, Manage, and Maintain Them
For Contractors This Is How to Get Your Small Business Ready for 2026 It’s time to separate your business and personal bank accounts.
Future of Work How the Telehealth Contractor Market Has Changed Since 2020 Telehealth Today Looks Very Different—Here’s How That Matters For Your Business
Compliance Scale Without the Year-End Data Consolidation Burden: Why November Matters How to eliminate weeks of manual reconciliation and ensure seamless January filing
For Contractors What Contractors Need to Know About the 1099-K Heads up: the reporting threshold is changing for 2025 and 2026.
For Contractors How New Changes to the 1099-NEC Will Affect Contractors Are you a contractor earning more than $600 per year? This affects you.
Payments Managing the New Behavioral Health Workforce: 1099 Compliance and Care Delivery at Scale The Rise of 1099 Provider Networks in Behavioral Health—and How to Manage Them
Compliance The 7 Pain Points That Make January 1099 Season a Nightmare (And How to Eliminate Them) Stop scrambling every January: automate the manual work now and walk into tax season completely prepared
Compliance These Are the Biggest 1099-NEC Filing Challenges (And How to Solve Them) Hint: the solution involves automation.
Compliance Stop Chasing W-9s: Why Smart Companies Automate Contractor Validation Before Tax Season The hidden costs of manual W-9 collection and last-minute TIN validation errors: and how to eliminate both
Future of Work How to Build HR Platforms for the New Workforce Reality Webinar Recap - Don’t Make Contractors an Afterthought
For Contractors Why Liability Insurance Is Worth Buying for Claims Adjusters It’s always good to have back-up.
For Contractors Why Contractors Should Consider Accident Insurance Reason #1: Occupational Accident Insurance can reimburse lost income
Future of Work Don’t Make Contractors an Afterthought How to Build an HR Platform for a Mixed Workforce
Updates Wingspan Raises $24M Series B to Scale Embedded Contractor Management and Capture $1.4T Market Series B led by Touring Capital will propel Wingspan’s mission to make flexible work effortless
Updates Insperity Partners with Wingspan to Launch First Contractor Management Solution Enabling Seamless Onboarding and Payments for Thousands of 1099 Workers
Updates Introducing Wingspan Embed: Power Contractor Management Directly Within Your Platform Legacy HR Systems Weren’t Built for the Modern Workforce
Updates Q2 Product Release Recap From ID Verification to Approval Workflows: Here’s What We Shipped in Q2
Customer Stories 2 Days → 2 Hours: How 3 Businesses Completely Transformed Their Payroll Process 3 Payroll Experts on Streamlining Their Payout Process
Customer Stories How to Onboard Contractors Twice as Fast 3 Experts on How to Onboard Your Contractors Faster
Future of Work Wingspan vs. Unit: Banking Built for Contractors Why You Should Partner with Wingspan for a Better Banking Experience
Future of Work Wingspan vs. Stripe: How to Build a Better Payments Process Why You Should Partner with Wingspan for a Better Payments Process
Payments You need more than just payroll to manage your contractors Why you need a comprehensive contractor management platform
Payments Embedded Finance Made Easy with Wingspan Add 1099 Capabilities to Your Software with Wingspan
Compliance What Claims Companies Need to Know About Tax Season Streamline Tax Compliance for Claims Adjusters: Simplify Your 1099 Process This Season
Onboarding Onboard Your Contractors in Weeks, Not Months with Wingspan How These Contractor-Built Businesses Onboarded Their Customers in Record Time
