The Story of Wingspan: Building the Operating System for the Future of Work

Sometimes the most compelling startup ideas come from experiencing a problem firsthand. In a recent episode of Category Visionaries, Anthony Mironov shared how his personal struggles as a freelancer led to founding Wingspan, a company reimagining how businesses manage and pay their contingent workforce.

From Private Equity to Personal Pain Point

Before founding Wingspan, Anthony’s career in private equity gave him unique insights into the payroll industry. “I evaluated over 30 investment opportunities in the peo space due to small business payroll and benefits, which ultimately culminated in a successful sale to Paychex,” he explains. This experience taught him “how incredibly important somebody’s paycheck is to the fabric of our society.”

But it was his subsequent experience as an independent consultant that revealed the true depth of the problem. “I experience firsthand the pains and frustrations of which tens of millions of Americans face,” Anthony recalls. The challenges were numerous: chasing late payments, cobbling together benefits from various providers, and struggling with tax compliance.

Deep Customer Research Shapes Early Direction

Rather than immediately building a solution, Wingspan invested significant time understanding the freelancer experience. “I remember three hour ethnographies really learning about the freelancer journey,” Anthony shares. These sessions revealed a common pattern: “Folks were effectively getting a PhD in reverse engineering a paycheck and point solution was really addressing the problem at its root.”

This research led Wingspan to initially launch as a direct-to-consumer platform. While the product resonated with users – many early adopters still use the platform today – scaling proved challenging. The company discovered an interesting phenomenon during COVID: freelancers were forming informal agencies, leading Wingspan to develop split payment capabilities that would later prove crucial for enterprise customers.

The Pivot to Enterprise

In summer 2022, Wingspan made a strategic shift to focus on B2B customers. “We got our first B2B customer, I think it was in the summer of 2022, and we realized that model was a lot more repeatable, especially for a venture backed business,” Anthony explains. This transition required significant changes, particularly in go-to-market strategy and organizational capabilities.

The pivot proved successful because Wingspan had built something truly different from existing solutions. As Anthony explains, they’re “solving a very different problem that’s really service traditional w two payroll systems or accounts payable systems.” Their platform handles the entire lifecycle of contingent work, from onboarding and eligibility verification to payment processing and benefits administration.

Building for the Future of Work

Looking ahead, Wingspan’s vision extends far beyond payroll and compliance. “I’m confident we could be the largest financial services company in the world and definitely in the US,” Anthony states. He draws parallels to how Shopify transformed e-commerce and Square revolutionized retail payments, envisioning Wingspan as the platform that will do the same for professional services.

“There’s Shopify that’s really designed for e-commerce businesses and they built a really beautiful ecosystem for developers to build on top of their APIs,” Anthony explains. “Similar to that for folks that are selling their services in person. Square has built really beautiful ecosystems for merchants and for individuals.” Wingspan aims to create a similar ecosystem for professional services, building “a unified platform built on a really unique contractor graph that removes all of the administrative complexity of working for yourself.”

This vision resonates particularly strongly today, as the contingent workforce continues to grow. “One out of three people in America are feeling to some extent that’s supposed to be north of 50% of population in the next five to ten years,” Anthony notes. By building the infrastructure to support this transformation, Wingspan is positioning itself at the center of the future of work.