The workforce is in the middle of a huge transformation. I’m not talking about RTO mandates or remote work…I’m talking about the rise of independent contractors, which make up nearly a third of the U.S. workforce. In 2024, independent contractors were paid a collective $1.4 trillion, and experts predict that by 2035 up to half the workforce will have done some kind of contract work as part of their career.
That’s why I sat down with Greg Franczyk, CTO of Wingspan, to talk through this. Before Wingspan, Greg held leadership positions at Google and the Washington Post. Seven years ago, he co-founded Wingspan to address the needs of the rapidly growing contractor segment, and he’s very passionate about building technology that simplifies complex systems.
You can watch the full video of our conversation or read the full recap below.
Traditional HR tech isn’t ready for this kind of workforce change
On paper, this shift to independent contractors should be great. Everyone from carpenters to Uber drivers to software developers to accountants get to choose flexibility and work-life balance over traditional employment options, and companies get specialized talent with variable costs.
“We’re trying to manage a modern workforce without the right technology,” says Franczyk. “If you’re the head of HR and your CEO says, ‘We need to bring on contractors and we need them fast,’ your stomach drops a little bit, because deep down, you know your systems weren’t built for this. You smile and say ‘no problem,’ but it’s actually a big problem.”
There are four core capabilities that HR technology needs to serve contractors, in addition to the functionality they already have for your W2 workforce. That includes:
- Rapid onboarding: The wrong onboarding system can take weeks for a contractor to get started, when you needed them yesterday.
- Automation: You’re already buried in other HR work, so you don’t have time to manually process dozens of tax forms and contractor payments.
- Contractor-based workloads: These aren’t employees who are punching a time clock or have a set salary. Instead, they have milestones, deliverables, or project-based payments that you need to be able to accommodate.
- Compliance: Failing to get this right comes with hefty fines from the IRS and more.
…but traditional HR tech falls into two categories: Vendor management or employee payroll. Says Franczyk, “Contractors aren’t employees, so they must be vendors…but then you realize that your vendor management system was designed to onboard maybe five vendors a month, not dozens of individual contractors all at the same time. Then the panic sets in. Do these contractors need workers comp? Should I be doing background checks? Now you’re Googling IRS guidelines. Your CEO wanted to move fast, but now you’re moving fast toward an audit.”
Traditional HR platforms aren’t much better. “The platform collects a W9, great. It'll issue a 1099, wonderful. But then you start asking those hard questions again,” says Franczyk. “Can it verify a contractor's insurance? No. What if they get hurt on the job? Can it track milestones and deliverables? How do we know what we're paying for?”
That creates a major chaos monster, requiring HR teams to stitch together features from both platforms with Google Forms, spreadsheets, and Slack messages. It’s all one big mess.
From Chaos Monster → Happy Contractors
What if you had another option?
Instead of a chaos monster of trying to combine vendor management tools and traditional HR platforms together, you need a dedicated contractor management solution built with contractors in mind.
Wingspan sets up a single workflow that keeps track of everything you need from getting all of your contractors to sign their onboarding documents right away to including project-based payment workflows and offering financial benefits like automatic tax withholdings and lifestyle benefits like health insurance:
- Payments: Offer instant payment options or automatically generate invoices for you or your team with line item detail.
- Contractor Verification: Built-in background checks and eSignature to make contractor onboarding quick and easy.
- Tax Compliance: Automatically create 1099s based on billable hours and includes automated tax withholding for contractors.
- Contractor Benefits: Give your contractors health insurance and other premium perks that make them want to work with you long-term.
- Contractor Help Desk: Our team will handle the admin questions so you can focus on your own day-to-day tasks.
“No more January nightmares or IRS penalties. No more Googling contractor law. No more Dropbox chaos. And no more contract hell in your inbox,” says Franczyk. “By bringing everything you need in one unified platform, we solve the contractor problem.”
Wingspan is Designed for Contractor Management
The workforce has already changed, and your systems need to catch up.
“Dedicated contractor management can become your competitive advantage,” he adds. “The companies that get contractor management right get the best talent, they scale faster, and they sleep better at night.”
If you’re struggling with managing your contractors, give Wingspan a try. We’ve helped our clients onboard thousands of contractors, reducing support time and taking care of their independent contractors. See how we can help you >
If you’re an HR platform, we’d love to talk more about embedding real contractor management solutions into your features so your clients can be ready for the future of what work looks like. Partner with us >
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