What services does Wingspan offer and what is the story behind its founding?

I spent the majority of my career working in payroll and benefits for small businesses. 

I became a freelancer myself at the end of 2016, and quickly realized that I could earn a great living working on my own terms. But it was really, really difficult. I started Googling: “How do you send an invoice? What's a contract? How do you piece together these disparate insurance providers like Oscar and Guardian?” 

When tax season came around, I had to basically lock myself in a room for a week to reconcile my entire life. 

I did that for a few cycles, and it opened up my eyes to this real pain point within the massive population that’s untethering from traditional employment structures—a pain point that has historically been solved by the traditional W2 paycheck.

As a full-time employee, you get paid every two weeks. Your taxes are withheld. You have access to benefits and services provided by your company or the government in the US, and you're able to focus on the work. I've spoken to a couple thousand freelancers by now, and everyone kind of struggles with the same problem. They're reverse engineering a paycheck, trying to piece together infrastructure that nobody should be really building on their own.

Wingspan is a connected system between companies and freelancers that makes working with freelancers and contractors effortless. What does that mean? 

For companies, we automate onboarding, payments, compliance, and reporting. 

For individual freelancers, they get a beautiful operating system. Every time they get paid, they can automatically withhold for their taxes. We offer automated bookkeeping. We're also a licensed insurance agent, so we can provide them Fortune 500 company benefits. It makes both sides of this new working paradigm possible.