Wingspan, the first payroll platform purpose-built for flexible workforces, today announced it has raised a $14 million Series A led by Andreessen Horowitz, bringing its total capital raised to $23.5 million. Existing investors Distributed Ventures, Long Journey Ventures, Ludlow Ventures, and 186 Ventures also participated, as did founders of Warby Parker, Harry’s, Allbirds, TubeMogal, and Catalant. Wingspan will use the capital to expand its team as well as invest in its platform, which is already relied upon to pay and extend benefits for tens of thousands of independent contractors. “The future of work is already here,” says Andreessen Horowitz General Partner David Ulevitch, who has joined Wingspan’s Board of Directors. “And Wingspan has built the financial infrastructure to better enable it.”

“More and more companies rely on independent contractors to sustain and grow their businesses, but managing payroll and benefits for them is rife with challenges and headaches for both parties,” said Wingspan co-founder and CEO Anthony Mironov, whose previous experience in private equity was deeply rooted in payroll and benefits. “Though much has been written about the future of work, actually supporting it requires a paradigm shift in how companies efficiently engage with independent contractors at scale. The shift toward a freelance economy was intended to minimize overhead and maximize flexibility, but it has also ended up creating an administrative crisis. We built Wingspan to catch up with the Zeitgeist.”

Mironov and CTO Greg Franczyk, previously at Google Cloud and the Chief Architect at the Washington Post’s digital platform, founded Wingspan after seeing these challenges firsthand. One out of every three people in the American labor force is an independent contractor, and their work contributes more than a trillion dollars a year to GDP, according to a 2022 study. Despite this emerging new normal, there is no system of record to integrate these legions of workers with the businesses that rely on them. This dynamic puts a wasteful administrative burden on contractors and companies alike — for managing episodic payments, accessing benefits, and wrangling 1099 tax issues — in a world that still seems to operate around a biweekly paycheck. “By rationalizing the process through workflow automation,” says Mironov, “Wingspan is freeing up time and effort for the pursuit of real, creative enterprise.”

“Our partnership with Wingspan has been transformational,” said Lisa Zeeveld, CFO at BELAY Solutions, a 100% remote, leading virtual staffing solutions company that works with more than 6,000 people. “Previously, our workflow for managing contractors fell short of our vision, with an inefficient process that required cobbling together multiple systems. Wingspan has become the critical workflow engine to streamline the process for fast payments and efficient onboarding of contractors, which is a competitive advantage in today’s changing labor market.”

Founded in 2019 to remove the barriers that come with working for oneself, Wingspan accelerates payments and allows companies to work with contractors at scale. Wingspan is an all-in-one, scalable solution for companies to onboard, pay, and support contractors effortlessly. It typically saves companies $240 per contractor and 10 hours in time per week. With more than 20,000 members and hundreds of enterprise clients, Wingspan is expected to surpass one billion in contractor payments by the end of the year.

“The Wingspan team truly understands the myriad issues facing companies and independent contractors when it comes to timely payments and benefits accessibility,” says Andreessen’s Ulevitch. “We are proud to be investors in Wingspan as they use this round of capital to rapidly scale the business to meet the needs demanded by today’s workplace.”

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