Most companies will tell you they have contractor management under control. The data suggests otherwise.

Wingspan and Global Surveyz surveyed 500+ HR and finance leaders across multiple industries to understand how businesses are managing their contractor workforces — the tools they use, the time they spend, and the gaps between what contractors need and what companies are actually delivering. In short, the growth in contractor hiring has outpaced the infrastructure built to support them. 

Here are three key findings that stood out. To gain all the insights from the full report, be sure to check out The Future of Flexible Work.

The tools companies use to manage contractors were never built for the job

Our survey found that 95% of respondents rely on three or more tools to manage the contractor lifecycle, with 68% juggling between three and six platforms and 26% using more than seven. The more contractors a company hires, the more fragmented its toolset becomes: 50% of companies that spend $1M+ on contractors use more than seven tools (in low-spend companies, only 15% use more than seven). These tools were designed to solve one-off problems: a contract here, a payment there, a background check somewhere else. What they were never designed to do is work together seamlessly at scale.

The result is a patchwork system that creates as many problems as it solves — and only 18% of companies say they're very satisfied with how it's all working. As contractor headcount grows, that dissatisfaction compounds. Tools that are merely inconvenient at 50 contractors become a genuine operational liability at 500. The companies that recognize this early and invest in purpose-built infrastructure will be the ones that scale without friction.

The operational burden of managing contractors is bigger than most leadership teams realize 

There is a striking confidence gap at the top of most organizations. 73% of CFOs say they're very confident in their company's contractor management, but only 14% of Directors share that confidence — because Directors are the ones actually doing the day-to-day work.

The numbers behind that gap are sobering. 68% percent of teams spend 21 or more hours per month on compliance alone, while 60% spend the same on contractor support. And operations teams are more than twice as likely as any other department to exceed 81 hours per month on contractor-related work. This points to a significant drain on the people and departments that companies rely on to keep the business running. And it scales directly alongside contractor hiring, which the majority of companies say is set to increase in the next three years.

Contractors are dissatisfied — and they have options

66% of respondents identified speed and timeliness of payments as the top contractor complaint. For companies that rely on contractors to deliver billable work — which, per our survey, is 84% of respondents — that dissatisfaction is now a business risk. Skilled contractors can choose who they work with, and the quality of the payment experience can be what determines whether they come back. Slow payments, opaque invoicing, and a confusing onboarding process are the kinds of friction that push top talent toward competitors who have figured out how to treat contractors like professionals.

The good news is that the market is moving. 60% of companies are either planning to invest in or actively evaluating purpose-built contractor management solutions. The ones that act first will have a meaningful head start — not just operationally, but in their ability to attract and retain the skilled contractor talent that is increasingly central to how modern businesses grow.

Want the full picture? Read The Future of Flexible Work.