Don’t Make Contractors an Afterthought

I recently spoke at HR Tech 2025 about how the way we work is fundamentally changing—and why HR platforms need to catch up.

During the talk, “Contractors Aren’t an Afterthought: Building HR Platforms for the New Workforce Reality,” I covered why more workers are choosing independent paths, how that shift impacts HR teams, and what platforms need to build to keep up.

You can watch the video of the talk or read the full recap below.

Right now, we’re in the middle of a massive shift in the way we work today.

50 years ago, the average worker spent the majority of their career at one company, as a salaried, full-time employee. Today, the median job tenure according to the Bureau of Labor Statistics is only 3.9 years. And one third of the workforce—that’s 60 million Americans—did some kind of freelancing, consulting, or contract-based work in the last year. That’s $1.4 trillion dollars paid to independent contractors in 2024 alone.

This isn’t just a trend. Or just about gig workers and side hustles for folks hoping to pick up extra cash by driving for Uber. There has been a 70% growth in spending on mission-critical “professional staffing” from 2018—2022. By 2035, we expect 50% of the  workforce to have done at least some kind of contract work as part of their career. That includes software developers, marketers, graphic designers, accountants—skilled professionals building small businesses instead of clocking in and out every day for a single company. 

That means HR professionals will have completely different requirements than they have in the past. 

How Contractors Will Reshape the HR Function

When we think about the composition of your organization in the coming years, you’ll find more and more independent contractors as a key part of your story. 

But HR and finance professionals are stuck working with technology designed with either vendors or full-time employees in mind. You have two options for these systems:

• Vendor management systems are designed to onboard one or two vendors a month, and are built for companies that have their own accounting departments, not individual people to supply tax forms or insurance verification. Vendor management tools can pay contractors.  But, you’re missing the rest of the tools you need like W9 collection,  background checks, and insurance verification.
• Traditional HR platforms know how to do all the employee stuff, like onboarding, W-9 collection, and documentation management or What about trying to figure out how to pay your contractor based on a project deliverable or milestone? Or paying an international contractor? ? Good luck.

Now instead of having one place to get it done, you’re left stitching together bits and pieces of these two systems, scattering documents, payment records, and insurance information across systems, spreadsheets, or Google forms. Reporting? Laughable. 

Not only does this make your job difficult, it’s also putting your team at risk. An audit with a patched-together system like this won’t end well for anyone.

Contractors Aren’t Vendors And They Aren’t Employees

What HR professionals really need is a third option: A system designed to handle your contractors: A Purpose-built contractor management platform.

Dedicated Contractor Management software includes features like:

• Rapid onboarding: Get your contractors on the job as quickly as possible without missing crucial steps like TIN verification.
• Automation. You don’t have to manually process dozens of contractor payments and tax forms with the right software.
• Support for contractor workflows: These aren't employees punching a time clock. They have milestones, deliverables, project-based payments and you need payment and tracking accordingly.
• Compliance: Because getting this wrong is expensive.

You need a dedicated contractor management system to be able to effectively onboard, pay, and manage these contractors—so they can focus on the value they’re adding to your company instead of chasing paperwork issues or wondering when their next invoice will get paid.

Wingspan Unifies the Contractor Lifecycle

The workforce has already changed. Your systems need to catch up.

With Wingspan, your HR team can onboard, manage, and pay contractors with a dedicated contractor management system:

• 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.

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The companies that get contractor management right? They unlock access to the best talent so they can scale faster without needing to put in long hours or tear their hair out managing it all. 

This is your competitive advantage moment.

Learn more about how Wingspan can support your contractors>

And if you’re an HR platform, let’s work together >

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