At Touring Capital, we look to invest behind generational shifts that will reshape the modern workforce. We see the shift from full-time employment to contract work as one of these defining trends. As such, we’re thrilled to back Wingspan, the first payroll platform purpose-built for the future of contract work.
The full-time employee experience has been well-served by decades of investment in HR systems, payroll processors, and benefit platforms. Contractors, however, are navigating an entirely different reality: inconsistent payment cycles, fragmented compliance requirements, and a lack of financial benefits and protections. The result is a broken experience not just for workers, but for the companies that rely on them.
Wingspan flips this dynamic by offering a unified system of record tailored specifically to the contractor economy. For businesses, the platform dramatically reduces compliance risk, onboarding time, and administrative overhead, turning what is often a chaotic process into a streamlined workflow. For contractors, Wingspan offers fast and reliable payments, integrated tax support, and access to financial tools that have long been out of reach.
The opportunity here is massive. Contract work now accounts for roughly 40% of the U.S. workforce, with an estimated $1.4 trillion flowing to independent workers annually. By 2027, half of all Americans are expected to earn income through contract work in some form. Wingspan is starting with high-friction verticals where reliance on contractors is highest, industries like healthcare services, insurance, and professional services. These verticals alone represent a multi-billion dollar opportunity. As Wingspan expands, it has a clear path to support tens of millions of workers across all sectors.
Wingspan is building a network effect that gets stronger with every contractor and company onboarded. An average contractor works with multiple employers; every time they use Wingspan for one job, they’re more likely to request it for the next. As adoption compounds, Wingspan becomes the preferred system for both sides of the market, delivering better outcomes, cleaner data, and more robust financial products that benefit from scale.
What excites us most is how far the company has come in a short period of time. Since pivoting to focus on the enterprise buyer, Wingspan has grown 6x with best-in-class retention, expanding rapidly across a base of nearly 100,000 contractors. Employers using Wingspan are saving over 80 hours a month in administrative work, onboarding 4x faster, processing payments 7x faster, all while retaining contractors at a higher rate.
This traction is driven by an experienced and mission-driven team, led by Anthony and Greg, that deeply understands the complexity of the problem. We are excited about Wingspan’s long-term vision to serve as both the software backbone and the fintech engine for the contract workforce. As the company continues to scale with partners like Insperity and Velocity Global, we believe Wingspan is well positioned to define this new category.
We’re proud to partner with the Wingspan team as they build the infrastructure that will power the next generation of work!