Resource Library

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.

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

Why you need a comprehensive contractor management platform

Add 1099 Capabilities to Your Software with Wingspan

Streamline Tax Compliance for Claims Adjusters: Simplify Your 1099 Process This Season

How These Contractor-Built Businesses Onboarded Their Customers in Record Time

How to Digitally Transform Your Contractor Payment Process

How Telehealth Providers Can Simplify Tax Season—Simplify 1099 Filing with Automation to Save Hours and Eliminate Errors

A fast-growing telehealth enterprise needed a better way to manage the processes behind creating and delivering thousands of 1099 forms to its growing network of mental health providers around the country. They partnered with Wingspan to make it happen.

Webinar Recap: 3 Key Challenges with 1099 Filing (and How to Solve Them)

Why Outsourcing Isn’t the Answer for 1099 Filing

The Secret to a Smooth Tax Season? Your Onboarding Process

What Accounting Teams Need to Know About 1099 Filing Penalties

Avoid Penalties and Protect Contractor Relationships with a Streamlined 1099 Filing Process

Why Vendor Payment Systems Fall Short for Contractor Management—and How to Fix It

A Contractor’s Perspective on Getting Paid

Why Traditional Payment Processors Don’t Work for Contractor Management

Empowering the Future of Work: Why I Joined Wingspan to Revolutionize Contractor Payroll and Management

Streamline Your 1099 Filing: How to Tackle Tax Season Stress-Free for Your Contractors and Business

The Challenge of Contractor Payments: Transforming Invoicing into Payroll Efficiency

Finance and accounting experts talk 1099 onboarding best practices, red flags and more in this ultimate masterclass.

Powering the historic growth in telehealth adoption is a rise in independent providers that can directly connect with patients through digital health platforms.

There are a plethora of laws and guidelines you can use to determine whether you're properly classifying your workers.

It's easy to see why businesses are eager to work with independent contractors, but the consequences of misclassifying them can get expensive, fast.

This guide provides in-depth guidance for businesses looking to mitigate their compliance risk when working with contractors at scale.

Not sure whether to classify a worker as an employee or independent contractor? Use this IRS framework to help assess your misclassification risk.

CRU Group COO Bret Peiffer joined our Co-Founder & CTO Greg Franczyk to discuss how the innovative claims company transformed its business using Wingspan.

Delivering a seamless adjuster experience becomes a strategic imperative for claims companies seeking to retain and grow a 1099 workforce.

Between 2016 and 2018, Instacart didn’t pay its Washington, DC contractors tips from customers. These missed tip payments led to a $1.5 million penalty from the Attorney General’s office.

It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is.

I learned firsthand how stressful and complicated the 1099 filing process is when I became a freelancer at the end of 2016.

I wanted to take a quick moment and reflect back on 2023 at Wingspan, an unforgettable year of momentum, milestones and growth.

1099 filing season can be incredibly stressful for finance teams. Here's everything you need to know before the filing deadline

Get the inside scoop for new 1099 requirements and how world-class finance teams are using automation to simplify and expedite the 1099 filing season.

Get the inside scoop for new 1099 requirements and learn how world-class finance teams are using automation to simplify and expedite the 1099 filing season.

See how businesses use Wingspan to automate onboarding, invoicing, payments, compliance, and benefits for their clients and flexible workforce.

In his Forbes debut, our CEO Anthony Mironov makes the case for a paradigm shift in how companies engage with contractors at scale.

Fintechs that serve the gig economy are forced to contend with a fractured and diverse landscape. Relevant stakeholders range from gig worker-hiring firms, to HR professionals, to gig workers themselves; building out useful and scalable products requires playing 3D chess, keeping key user cases—as well as shifting regulations—top of mind

The brand strategist and copywriter shares the the best advice she’s ever gotten, plus the mindset freelancers must have to succeed.

The branding and marketing consultant shares her go-to inspiration, the best advice she’s ever gotten, and the one thing all freelancers must master.

The architect turned ceramicist is the founder of Not Work Related, a Brooklyn-based housewares company.

How to Manage Parental Leave with Contractors

A career coach shares her best tips.

The photographer, videographer, and composer produced the award-winning documentary “Big Charity."

Bonus: Your health and your productivity will soar.

Five foolproof ways to sell your services to a prospective client.

Advice from experts that help small business owners navigate (and overcome) seven thought patterns that can undermine our work.

These groups provide advice, collaboration, and even a source of new jobs.

It helps you stay legally compliant and protected. It also provides benefits to your customers and employees.

Commercial litigation attorneys John Thompson and J.R. Skrabanek specialize in helping freelancers, entrepreneurs, and startups collect on unpaid invoices.

The makeup artist has worked with Marc Jacobs, Parade, Susan Alexandra, Milk Makeup, Refinery29, Man Repeller and more.

Sidestep these common pitfalls.

He hired his former co-workers after he lost his job.

We're here to celebrate your ingenuity as a solopreneur.

Because discussing pay, workflow and other topics can be really awkward.

Work smarter – and more efficiently.

He describes his career as a “side hustle on steroids.”

Good news: this type of insurance may qualify you for a tax break.

Good news: it will accelerate your cash flow.

You'll need to pay self-employment taxes if you earn $400 or more.