From Ethnography to Enterprise: How Wingspan Turned Customer Research into Product-Market Fit

Most founders start with a solution in search of a problem. In a recent episode of Category Visionaries, Anthony Mironov revealed how Wingspan took the opposite approach, conducting extensive ethnographic research to uncover the deep-seated challenges facing independent workers before building their solution.

Starting with Deep Customer Understanding

Before writing a single line of code, Wingspan invested significant time understanding the freelancer experience. “I remember three hour ethnographies really learning about the freelancer journey,” Anthony shares. These in-depth sessions revealed a surprising pattern: “Folks were effectively getting a PhD in reverse engineering a paycheck and point solution was really addressing the problem at its root.”

Personal Experience Shapes Research Focus

Anthony’s background provided unique context for these research sessions. “I experience firsthand the pains and frustrations of which tens of millions of Americans face,” he explains. This personal experience, combined with his private equity background evaluating payroll companies, helped him recognize patterns in the research that others might have missed.

From Individual Pain Points to System-Level Insights

The ethnographic research revealed that freelancers’ challenges weren’t just about getting paid – they were about managing an entire business infrastructure. As Anthony notes, “I remember as a freelancer myself, chasing a client to pay me, or aggregating piecing together various insurance carriers like Oscar and Guardian, or locking myself in a room to reconcile my life to tax season, I was like, oh my God, this is crazy. There’s 60 million individuals that are struggling with this.”

COVID’s Impact on Product Development

The pandemic provided unexpected validation of their research findings. “During COVID we saw lots of freelancers were working together in like effectively many agencies,” Anthony explains. This observation led to the development of split payments functionality, which would later become a crucial feature for enterprise customers.

Translating Consumer Insights to Enterprise Value

The transition to B2B wasn’t about abandoning their consumer insights – it was about scaling their impact. “We service companies that are built on attention work,” Anthony explains. “These workers are really core to the business. So recruiting and retaining that talent is fundamental to these industries. So folks want financial and health benefits just like w two employees.”

Building Purpose-Built Solutions

Their deep understanding of freelancer needs helped Wingspan differentiate from legacy solutions. Anthony explains why their approach is unique: “The adps of the world were never really designed for this because the w two role is really, you set it and forget it. There isn’t the same lifecycle management aspect of it.”

From Research to Category Creation

Rather than fitting into existing categories, Wingspan’s research led them to create a new one. “We decided to really hone in on this lifecycle management of contingent work as the category that we are developed over time,” Anthony shares. This decision was directly informed by their understanding of both freelancer and enterprise needs.

The Impact of Deep Customer Understanding

The depth of their initial research continues to pay dividends. Their enterprise customers now use Wingspan as a recruitment and retention tool, with Anthony noting that “we oftentimes hear some workers won’t work with a company if they’re not on wingspan.”

This success stems directly from their commitment to understanding the fundamental challenges facing independent workers. By starting with deep customer research rather than predetermined solutions, Wingspan built a platform that addresses both individual freelancer needs and enterprise requirements – a rare achievement in B2B software.

For founders, Wingspan’s journey offers a powerful lesson: sometimes the best path to enterprise success starts with understanding individual users deeply enough to recognize systemic problems that businesses will pay to solve.