From an All-Day Payments Process to a Quick Morning Task: How Patriot Claims Consolidated Contractor Operations with Wingspan

Overview

Patriot Claims is a national network of claims inspectors who investigate wind and hail claims for insurance carriers across the country. When a hurricane hits the Gulf Coast or a hailstorm rolls through the Midwest, Patriot Claims dispatches its 1099 inspectors fast. The business model runs on rapid, bulk onboarding of new inspectors when catastrophic events strike, and those inspectors expect to be paid quickly once the work is done.

Running that kind of surge-driven contractor operation takes real infrastructure. Patriot Claims needed a platform that could handle inspector onboarding, payments, insurance verification, background checks, and multi-state 1099 filing in one place, without forcing their back office to chase contractors across spreadsheets and vendor portals. They chose Wingspan.

Challenge

Before Wingspan, Patriot Claims ran on WorkMarket for contractor payments and a patchwork of other vendors for everything else. The friction of managing fragmented systems showed up everywhere.

Payments were an all-day process. David Binns, Patriot Claims' Chief Financial Officer, inherited the workflow when he joined the company. Every pay period, the team compiled inspector pay data into a spreadsheet and uploaded it to WorkMarket. The friction stacked up from there. Payment deductions couldn't be entered as negative numbers, so workarounds piled up for routine fee recoupments. When the upload failed, WorkMarket flagged the error but didn't say which line in the file caused it. The team had to dig through the entire file row by row to find the bad data. "It was very cumbersome," David says. "If you missed something, you'd have to go through and do the whole upload again." Even pulling a clean payment report was a project in itself. Jarrod Ham, President of Patriot Claims, likened the reporting experience to working through a convoluted algebra problem.

The COI side was worse. With inspectors spread across 38 states, keeping insurance coverage current was a constant chase. "It was a disaster to track," says Jarrod. "You'll get 30 inspectors that send it in, and they say, 'hey, we've sent it,' and we haven't received it. You're chasing your tail all the time." WorkMarket's reports listed "yes" or "no" for coverage, with no dates attached. A contractor could show as "yes" while running a policy that had lapsed weeks earlier.

And the vendor stack was sprawling. Patriot Claims was managing background checks, COI collection through separate vendors, with WorkMarket tracking coverage status on top of running payments. Each system had its own login, its own report, its own version of the truth. 1099 season made the fragmentation visible. The first year of filing across split systems was its own project.

Solution

Patriot Claims chose Wingspan to consolidate all contractor work in one place. Inspector onboarding, payments, COI tracking for general liability and workers' comp insurance, background checks, and multi-state 1099 filing now all run through Wingspan. The HubSpot integration syncs new inspectors automatically, so when a catastrophic event triggers a surge of dispatches, the back office can keep up without running setup work across multiple vendor portals. And because Wingspan validates every COI by confirming it matches the inspector's name, is active, and carries the required coverage limits, the back office stays confident in its coverage even when inspectors work claims across half a dozen states in a single deployment.

Impact

Payments Run in Hours, Not Days

Under WorkMarket, payments were an all-day process. With Wingspan, the same workflow is now much more efficient, and the team has recovered roughly 2 hours a month on invoice processing alone. "I can do it in two or three hours," David says. "It's made it much more efficient and cleaner."

Patriot Claims funds payments through the Wingspan Wallet, so inspectors get paid the next business day after every run. Pay lands about 2 hours faster than it did under WorkMarket. The team processes payments on Thursdays, and inspectors see their pay hit their accounts Friday.

Errors Don't Mean Starting Over

A single payment error used to mean restarting the entire upload from scratch. Wingspan ends that. The platform flags the specific payment entry that's off and tells the team exactly what's wrong, so they can fix one line and resubmit. "When you do an upload, it will tell you instantly which ones are off," David says. "You go look at the file, okay, that's why it's off, you update the file and re-upload." Payment errors are down 5% since the move to Wingspan, and the rare ones that do happen get fixed in minutes.

Insurance Built into Onboarding

Patriot Claims inspectors have three paths to coverage through Wingspan. Inspectors who need coverage can enroll directly in Wingspan’s master policies, Occupational Accident Insurance (OAI) for work-related injuries, and/or Professional & General Liability (PL/GL) for comprehensive liability coverage. Those who already carry a policy can simply upload their own COI. Or they can connect with Wingspan’s partner broker, Equal Parts, to source a policy of their own. Wingspan holds the master policies, and enrolled inspectors are covered as members.

Once an inspector is covered, Wingspan tracks the policy in real time. Expiration dates, policy validity checks, and automatic reminders all run in the background, so inspectors stay current and compliant, and the Patriot Claims team knows immediately if any coverage lapses.

Previously, inspectors had to bring their own insurance. Now, a new inspector who clears every other requirement can get coverage as part of the same onboarding flow that sets them up to get paid. There’s no separate insurance step, no waiting. When a storm hits and Patriot Claims needs to ramp the field fast, insurance acquisition isn't the bottleneck.

"The ability to get workers' comp and general liability for our inspectors, Wingspan helped tremendously with that," Jarrod says.

Tax Withholding for Inspectors

Inspectors can opt to have taxes withheld directly from their pay at no cost to them, a free Wingspan feature that wasn't available under WorkMarket. It gives 1099 inspectors something W-2 employees take for granted: no surprise bill at tax time. “It’s super. We love it,” Jarrod says.

1099 Filing Runs in One Morning

Year-end used to mean reconciling payments across two systems and waiting for corrections to push through. With Wingspan, the same workflow runs through a single platform. Between validating and sending 1099 forms and resolving downstream issues, the team saves 16 hours during tax season, and a 25% drop in the 1099 error rate means fewer corrections in the first place. "Filing's been a night and day difference," David says. "It's literally a morning run, much more efficient, much cleaner."

Looking Forward

Patriot Claims continues to add new insurance carriers and scale its inspector network. The team is rolling out an internal claims management system that will feed payment data directly into Wingspan, cutting the manual upload step entirely. As the business grows, the Wingspan partnership grows with it.

“It's a day in time that people get back. And then you add on top the insurance that's needed by the contractors, the 1099 reporting. It's much more efficient and the reporting is much easier.” — David

Patriot Claims runs on the ability to scale up the moment a storm hits. Wingspan keeps the back office ready for it, giving the team back 20 admin hours a month, and confident that every inspector in the field is covered by a valid, verified policy before they ever work a claim.

See why leading operations teams trust Wingspan to handle contractor onboarding, payments, 1099s, and compliance at scale. Request a Demo →