Wingspan is the first modern payroll platform built for independent contractor management, offering onboarding, tax automation, payments, and optional insurance products. It provides platforms and their customers with tools to manage contractors at scale, ensuring timely payments and simplified onboarding. In under three years the company expanded its customer base by 200%, increased average ACV fivefold, supported 12x more contractors, and processed over $3B in payments. Wingspan's product is used across industries — including Omni's gig workers, CRU Group's insurance adjusters, and 10,000 providers at Teladoc, which reports an average savings of 28 hours per month on payment processing. The company has launched Wingspan Embed, an embeddable API-first solution that brings contractor onboarding, tax withholding, payments, debit cards, instant payouts, and insurance to HCM and HR platforms. Wingspan plans to use new capital to accelerate Embed adoption, expand in healthcare, insurance, staffing, and professional services, invest in its team, and launch AI-powered products to automate compliance and payments. Wingspan provides an all-in-one platform that consolidates onboarding, payroll, benefits and contractor management for mid-market employers working with freelancers. The product offers email-based contractor invitations, background checks, same-day payments, self-service W-9 and e-signature collection, and automated 1099 generation and filing. Wingspan uses AI and machine learning to auto-categorize expenses and streamline contractor data maintenance, acting as a system of record with a company-contractor graph to speed repeat payments. The platform also offers contractors access to discounted health, vision, dental and life insurance. The company says it has more than 20,000 members, “hundreds” of enterprise clients and is on track to surpass $1 billion in contractor payments by year-end. Wingspan, founded in 2019, plans to expand the product and double its ~20-person team by the end of the year.

Total raised

$38M

Funding rounds

2

Latest round

Series B

Latest activity

Jul 2025