Resource Library

Prepare, approve, fund, and reconcile a bulk contractor payment run with checks for duplicate work, rate changes, and failed payments.

Use a practical COI review checklist to define contractor insurance requirements, route exceptions, track renewals, and retain clear decisions.

Evaluate contractor portals for payment details, secure profile updates, tax documents, correction requests, and support with this buyer’s checklist.

Build a creator payment workflow that connects deliverables, fee approvals, payout status, tax records, and accounting with practical handoff templates.

Plan embedded contractor onboarding and payments with an ownership map, record checklist, webhook recovery tests, and launch criteria.

Plan international contractor payments with a country worksheet, fee comparison, tax-document checks, exception process, and reconciliation guide.

Design recurring contractor payment schedules, handle variable amounts and missed cutoffs, and approve off-cycle payments without duplicates.

Check onboarding progress, prepare payables, and understand payment history through Claude and ChatGPT. Your team keeps final payment approval and execution in Wingspan.

This quarter, Wingspan Embed covers the full contractor journey, bulk approvals run in the background, requirement edits keep a full history, and failed payments finally explain themselves.

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.

A customer spotlight conversation with Durga Arjun, VP of Provider Operations at Blossom Health, on consolidating a fast-scaling 1099 psychiatry telehealth platform and delivering W-2-grade benefits to a growing provider network.

W-2 payroll and 1099 contractor management, together in Wingspan.

“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.

Compare contractor payroll and management platforms across onboarding, payments, 1099 compliance, global reach, integrations, and contractor experience.

Let’s learn the basics.

Compare contractor management software with a weighted buyer's scorecard, practical demo tests, customer examples, and a total cost checklist.

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.

Build a W-9 collection and TIN matching workflow with clear owners, secure updates, mismatch resolution, and records ready for 1099 review.

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 2025

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

Compare Wingspan and Stripe Connect for contractor onboarding, payments, tax reporting, support, and the work your team will own.

Compare one payroll platform with connected systems for employees and contractors. Use a decision matrix for tax, operations, and reporting.

Add 1099 Capabilities to Your Software with Wingspan

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

Plan a contractor payment platform migration with data mapping, a representative pilot, tax-history checks, and clear go-live criteria.

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)

Compare 1099 software, outsourced filing, and hybrid workflows with an ownership map, cost worksheet, and practical tests for data and corrections.

The Secret to a Smooth Tax Season? Your Onboarding Process

Understand 1099 filing penalties by return due year, separate IRS and recipient obligations, and follow a practical process for missed or incorrect forms.

Choose between 1099-NEC, 1099-MISC, and 1099-K using payment type, 2026 thresholds, reporting responsibility, and the correct filing deadlines.

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

Compare ACH and eligible instant payouts, shorten approval delays, plan funding, and resolve exceptions without losing payment controls.

Use a contractor onboarding checklist with owners, evidence, exception paths, and readiness checks for finance and operations teams.

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

Understand the IRS, federal wage-and-hour, and state worker classification tests, with current rule context and a practical evidence checklist.

See how worker misclassification costs can include taxes, wages, contributions, damages, and state penalties, with a practical exposure-review worksheet.

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

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

How to Manage Parental Leave with Contractors

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

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

Good news: it will accelerate your cash flow.