Articles

A Guide to Paying Freelancers and Staying Compliant (2026 Edition)

“When will I get paid?”

Your contractor workforce is scaling. The systems running it aren't.

60% of the companies we surveyed are taking action.

It starts with onboarding pain, but it doesn’t end there.

Not every contractor living abroad should be treated as an international payee.

Managing contractor work hours shouldn't require spreadsheets, separate time-tracking tools, or support tickets.

It’s a serious operational burden.

For them, it’s more than a gig.

Discover how a purpose-built system ensures compliance, speeds up payments, and protects your bottom line.

A contractor management crisis is hiding in plain sight.

At Wingspan, we’re focused on solving the unique needs of contractors across the entire management lifecycle.

Some states are not like the others.

Why Modern Enterprises are Moving Beyond Manual Payroll

Let’s learn the basics.

Move beyond legacy AP tools and discover how modern platforms automate compliance, accelerate onboarding, and unlock the full potential of your contingent workforce.

Expect the unexpected.

What Economic Upheaval, AI, and Changing Regulations Mean for Your 1099 Workforce

The next payment is due sooner than you might think.

Want to streamline your operations, learn new skills, and spark creativity? Start here.

These highly skilled professionals are the future of the modern workforce.

Your next side hustle could start today.

Here’s a look at what’s new at Wingspan

4 Experts Predicted These Top Trends for 2025 - How Did They Do?

There are no dumb questions here.

‘Tis the season.

How to Build, Manage, and Maintain Them

It’s time to separate your business and personal bank accounts.

Yeah, it’s tax time already. Again.

Telehealth Today Looks Very Different—Here’s How That Matters For Your Business

How to eliminate weeks of manual reconciliation and ensure seamless January filing

Heads up: the reporting threshold is changing for 2025 and 2026.

Are you a contractor earning more than $600 per year? This affects you.

The Rise of 1099 Provider Networks in Behavioral Health—and How to Manage Them

Stop scrambling every January: automate the manual work now and walk into tax season completely prepared

Hint: the solution involves automation.

The hidden costs of manual W-9 collection and last-minute TIN validation errors: and how to eliminate both

Here’s a look at what’s new at Wingspan

Webinar Recap - Don’t Make Contractors an Afterthought

It’s always good to have back-up.

Reason #1: Occupational Accident Insurance can reimburse lost income

How to Build an HR Platform for a Mixed Workforce

Series B led by Touring Capital will propel Wingspan’s mission to make flexible work effortless

Enabling Seamless Onboarding and Payments for Thousands of 1099 Workers

Legacy HR Systems Weren’t Built for the Modern Workforce

From ID Verification to Approval Workflows: Here’s What We Shipped in Q2

3 Payroll Experts on Streamlining Their Payout Process

3 Experts on How to Onboard Your Contractors Faster

Why You Should Partner with Wingspan for a Better Banking Experience

Why You Should Partner with Wingspan for a Better Payments Process