Investing in Wingspan

The contractor payroll market is massive. Roughly one-third of U.S. workers have performed freelance work in the last year, and $1.4 trillion is paid out to contract workers annually. In many ways, contractors are the backbone of the U.S. economy. When an earthquake damages your house, the inspector who comes to assess it is often an independent contractor. When you’re spinning up a new small business and hire a consultancy firm to help with marketing strategy or SEO, that person is often self-employed.

And, yet, contracting, and working with contractors, remains a challenge. Things like payroll, insurance, and tax withholdings are pretty simple for W-2 employees, but every step is far more complicated when it comes to independent contractors who are paid project-by-project and are often classified as sole proprietorships. For the employer working with the contractor, onboarding workers and ensuring they’re fulfilling all legal and compliance obligations is a never-ending headache, given they have to go through the process repeatedly with each contractor on each project. Moreover, being able to actually pay the contractor — calculating what the contractor is due by project, properly calculating the corresponding taxes, and then actually disbursing the money (often through paper checks, or through if they’re more digital) — is a logistical nightmare. 

Contractors have the inverse set of problems around managing payments. These workers are often sole proprietorships — they have to track their own pay, physically deposit paper checks, manage separate personal and business finances, calculate taxes (which are far more complicated for contract workers), and figure out their own insurance and benefits. All in addition to actually doing the work for which they’re being paid. 

Luckily, Wingspan is here to solve this headache for all parties. Wingspan serves as a business’s system of record to manage independent contractors. Through Wingspan, businesses can easily manage the onboarding and training of these workers, track their jobs (and, thus, how much they need to pay out), and properly calculate taxes and generate compliant tax forms. 

These businesses then roll out Wingspan’s contractor-facing app to the contractors, who can use it to manage everything about their sole proprietorship. Through Wingspan, they can get instant payouts, 1099 tax support, debit cards, business banking accounts, and referrals to benefits not provided by their contract employers, instead of having to set up their own business bank account, manage their own expenses, and cobble together QuickBooks, TurboTax, etc. It’s far simpler for them to get access to these services through Wingspan directly in their employer app, rather than find these solutions on their own.

When we first met the Wingspan team, it was clear they were solving an incredible pain point for users. We talked to customers, and heard time after time how incredible Wingspan has been for them and for their independent contractors, some of whom said they’d never again work for an agency or employer that didn’t use Wingspan. Further, many of the contractors on Wingspan’s platform take advantage of one of its financial solutions. 

Anthony Mironov and Greg Franczyk are purpose-built to solve this problem. Anthony worked with professional employer organizations in his prior career in finance and experienced the challenges of working as a freelancer firsthand. Greg, too, had seen the pain points — his wife is a freelancer — and his experience in building large-scale systems as the former chief architect at the Washington Post, and previously working at Google Cloud, drew him to the technical challenge. We heard from customers consistently about how great they’ve been to work with and how deeply they empathize with customers’ pain.

We’re thrilled to lead Wingspan’s Series A and help them achieve their vision of providing the first purpose-built payroll platform for independent contractors. They’re hiring!


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