Somewhere right now, a finance manager at a healthcare company is not generating 10,000 tax forms by hand. She is not chasing W-9s over email, not reconciling a spreadsheet of bank details, not staying late in January to mail 1099s. The work still happens - it just happens inside Wingspan, in the background, the way good infrastructure is supposed to.
Wingspan sells the least glamorous product in software: paperwork that pays people. It is a payroll and management platform built for the one part of the workforce that payroll software historically ignored - the 1099 contractor. In 2025 the company raised a $24 million Series B and started shipping that whole machine as an embeddable API, so other companies can drop it into their own products. Roughly 130 people, scattered from New York to Poland to India, keep $3 billion in contractor payments moving.
Here is the number that started it. Americans are paid about $1.4 trillion a year as contractors - roughly 4% of GDP, spread across an estimated 74 million people. By Wingspan's reading of the trend, close to half of US workers will earn some independent income by 2027. A workforce that large should have serious infrastructure behind it.
It mostly doesn't. Hiring a contractor means collecting a W-9, verifying identity, maybe running a background check, wiring money, tracking what you paid, withholding nothing (that's the contractor's problem), and then - months later - producing a correct 1099 for every single one. The tools built for W-2 employees don't fit. So companies improvise with spreadsheets, manual transfers, and a January scramble that nobody enjoys and auditors enjoy even less.
Greg Franczyk, who would become Wingspan's CTO, had led engineering at The Washington Post and managed a team at Google - he knew what real infrastructure looked like. Anthony Mironov had spent his early career on a private equity desk, close enough to small-business payroll and benefits to see how badly the contractor side was served. They were looking at the same gap from two directions.
In 2019, Mironov and Franczyk made a specific bet: contractors didn't need a nicer invoice button. They needed a system of record - one place that held the identity, the documents, the payments, the taxes, and the benefits for an entire flexible workforce. Do that, and you don't just process a transaction. You own the relationship.
The clever move was making the contractor do the data entry. Onboarding flips the usual burden: the worker adds their own bank account, signs their own documents, and uploads their own W-9. The company just sends an email invite. It's the kind of design choice that sounds minor and quietly removes the single most painful step in the whole process.
Andreessen Horowitz bought the thesis, leading a $14 million Series A in 2023. The line from a16z's David Ulevitch is about as blunt a bet as a venture firm makes out loud: every platform will need a contractor stack, and the smart ones will embed Wingspan. That sentence, it turns out, was also a product roadmap.
The core product handles the full contractor lifecycle so a company doesn't have to stitch five tools together.
Invite a contractor with an email. They add their bank account, W-9, e-signed docs, and clear a background check themselves.
Consolidated payables and same-day payments, plus the Wingspan Wallet with instant payouts and a spend card.
Automated 1099-NEC workflows that estimate withholdings, surface write-offs, and file forms for the payer.
The 2025 launch: an API-first, white-label contractor stack - withholding, debit cards, instant payouts, insurance - dropped into HR, HCM, and PEO platforms.
The business model is the unglamorous, durable kind. A monthly platform fee, a per-contractor fee of around $5, and then a long tail of financial-services economics - float on payments, markups, and roughly $1.05 of card interchange for every $100 a contractor spends. Reported gross margins sit near 80% with retention around 90%. Wingspan is careful to note it is a fintech company, not a bank.
Skeptics, fair enough - lots of fintechs describe a trillion-dollar market and then process a rounding error. Wingspan's growth in the run-up to its Series B is the part that gave Touring Capital conviction to lead.
The customer list reads like the messy edges of the economy where contractors actually live: Teladoc Health in telehealth, CRU Group's insurance adjusters, Omni's gig workers. Then Insperity - a PEO giant - picked Wingspan to power its first contractor management solution. That partnership is the embedded thesis proving itself: not Wingspan reaching every company, but every company reaching contractors through Wingspan.
Strip away the API talk and the mission is simple enough to fit on a sticky note: make contract work effortless for the businesses that hire contractors and for the contractors themselves. The second half matters. Independent workers rarely get benefits, instant pay, or anyone handling their taxes. Wingspan folds discounted health, vision, dental, and life insurance into the same platform that pays them.
Wingspan is betting that contractor infrastructure becomes a default expectation, not a feature - the same way nobody builds an app today without a payments processor underneath. If they're right, the company most people will never knowingly use ends up touching a large slice of how Americans get paid.
The road isn't empty. Deel and Remote come at contractors from the global-hiring side. ADP, Gusto, and Rippling own employee payroll and could lean in. Bill.com and Brex sit on the payables flow. And a new crop of API-first infrastructure players - Check, Zeal - want to be the layer underneath everyone. Wingspan's edge is focus: it built for the 1099 worker specifically, then turned that into something other platforms can rent.
That's the whole bet, really. Not that contract work is the future - everyone says that. It's that someone has to make the future's paperwork disappear, and Wingspan would rather it be them, quietly, in the background, one automated 1099 at a time.