Wingspan

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.

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.

“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.

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

3 Experts on How to Onboard Your Contractors Faster

3 Payroll Experts on Streamlining Their Payout Process

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

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.

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.

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.

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

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