Contractor payroll sounds simple until you actually try doing it. Ask any company scaling fast and swimming in 1099s. Ask the finance lead who hasn’t slept since Q4. Ask the ops team duct-taping Excel sheets to keep payments moving. That’s the noise Wingspan tuned out from day one, and today, they just turned the volume up with a fresh $24M Series B to keep rewriting how modern workforces get paid and stay compliant.
Led by Touring Capital with returning believers Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures, and 186 Ventures, this round brings Wingspan’s total raise to $54M. The backing isn’t just about capital, it’s a sign the smart money sees what’s next: a contractor economy that isn’t niche anymore, but foundational. It’s not side hustles anymore. It’s main income. And it’s only growing louder.
Co-founders Anthony Mironov (CEO) and Greg Franczyk (CTO) weren’t chasing hype, they were solving the broken bits freelancers and enterprises both hated. Payment lags. Tax chaos. Onboarding that felt like digital origami. What they built wasn’t a patch, it was a platform. End-to-end lifecycle management for contractors, from real-time W9 collection to instant payouts and 1099 filing. The result? Over $3B in payments processed. 12× contractor growth. A 5× boost in annual contract value. And names like Teladoc Health trusting Wingspan to manage 10,000 providers, and saving 28 hours a month doing it.
But the real mic drop? Wingspan Embed. A modular, API-first toolkit sliding seamlessly into HRIS and HCM systems. Think embedded contractor management that doesn’t need a replatform or reorg. Just clean, quiet integration that makes ops teams breathe easier and finance folks stop grinding their molars.
This Series B isn’t about maintaining. It’s about multiplying. Wingspan is scaling its embedded infrastructure across verticals like healthcare, staffing, and professional services, where flexibility is gospel but compliance is non-negotiable. The team’s loading up on engineering, product, and AI talent to drive the next era of automated compliance and real-time contractor management. Because the future isn’t employees vs contractors. It’s optionality. Fluidity. It’s having the infrastructure to scale whoever, whenever, with zero friction.
Congrats to Anthony Mironov, Greg Franczyk, and the Wingspan crew. This isn’t just a fintech story. It’s a workforce movement.
Touring Capital, Andreessen Horowitz, Distributed Ventures, Long Journey Ventures, Company Ventures, 186 Ventures, you saw it before the chorus kicked in.
The rest of the room just turned to listen.
Startups Startup Funding Venture Capital Series B Payroll Payroll Tech Workforce HR HR Tech FinTech Infrastructure Compliance Technology Innovation Tech Ecosystem Startup Ecosystem Hiring Tech Hiring
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