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Delivery & Courier Services
Pay drivers the day work is done — not two pay cycles later.
Wingspan handles driver onboarding, per-delivery payments, compliance tracking, and 1099 filing for last-mile delivery platforms and courier networks. One platform built for companies managing 100 to 10,000+ independent drivers.
$1.5M+
Moved to drivers monthly across Wingspan delivery network customers.
Monthly driver pay
40,000+
DeliverThat manages 40,000+ independent drivers on a single Wingspan platform.
Drivers managed
Same-day
DeliverThat moved from twice-weekly ACH to same-day driver pay, cutting payment support tickets.
Pay available
Trusted by businesses that run on contingent work
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Onboard new drivers in hours, not days
Wingspan replaces the disconnected stack of recruiting tools, form flows, and Zapier integrations with a single onboarding workflow. Drivers complete W-9s, license uploads, insurance verification, and background check consent from their phone.
Embed the entire experience inside your driver app — drivers never see Wingspan branding, only your interface. As you grow from 500 drivers to 5,000, onboarding scales without adding headcount.
Pay drivers when the delivery is confirmed, not days later
Wingspan connects to your dispatch data so payments trigger automatically when a job is marked complete. Drivers get paid same-day and you eliminate the manual ACH upload cycle.
Drivers access their pay through a branded portal where they view pay history, download 1099s, update bank information, and request instant transfers. Your support team stops fielding "where's my money?" tickets.
File 1099s for thousands of drivers without a spreadsheet
Every disbursement is tracked per driver throughout the year. When filing season arrives, Wingspan generates 1099-NECs automatically.
No manual export, no reconciliation against separate systems, no February scramble. TIN validation runs at onboarding so mismatches surface before the first payment — not in January when corrections cost time and penalties.
Track licenses, MVRs, and insurance before a driver gets behind the wheel
An expired license, a lapsed auto insurance policy, or a failed motor vehicle record check is not just administrative — it is a liability event. In California, AB5 adds misclassification exposure that requires documented independent contractor relationships.
Wingspan tracks every credential with automated expiry alerts, and Wayfinder AI verifies documents on submission, catching mismatches before a driver is activated. You get a defensible compliance record for every driver in your network.
Managing payments for thousands of delivery drivers used to consume our finance team's entire week. Automating contractor payments freed us to focus on scaling the business.
Operations Director
National Delivery Network
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