The Hidden Toll of Managing Contractors at Scale

Ask a CFO how contractor management is going at their company and you'll likely hear that things are under control. Ask the managers doing the day-to-day work and you'll hear something very different. This confidence gap – and the operational burden hiding beneath it – runs deeper than most leadership teams realize.

Wingspan and Global Surveyz surveyed 500+ HR and finance leaders to understand more about what managing contractors looks like in 2026 and beyond. Below are key insights from the report related to how companies currently manage contractors. For all the report’s takeaways – including findings related to contractor hiring and retention – download The Future of Flexible Work report.

Leadership and the people doing the day-to-day work see things differently

The disconnect between executive confidence and on-the-ground reality of contractor management is stark:

• 73% of CFOs say they're very confident in their company's contractor management
• Only 14% of Directors share that confidence
• Managers are most likely to cite onboarding clarity as a top contractor complaint: 42% vs. 29% overall
• Managers also lead on invoice management dissatisfaction: 36% vs. 23% overall

When leadership is this disconnected from the daily reality of contractor management, process failures often go unfixed, and get exponentially worse as contractor rosters expand.

Companies are managing contractors with a fragmented toolset

The current tooling situation at most companies is a direct reflection that contractor management is treated as an afterthought, solved one problem at a time.

• 95% of respondents use three or more tools to manage the contractor lifecycle
• 68% juggle between three and six different platforms
• 26% use more than seven tools
• Only 18% of companies say they're very satisfied with their current contractor management processes

These tools were each built to solve a specific problem – a contract here, a background check there, a payment somewhere else. Stitching them together creates operational complexity that compounds as contractor headcount grows. Among companies spending $1M or more on contractors, half rely on seven or more tools – a rate more than three times higher than lower-spend companies.

The time burden is substantial – and spans every department

Managing contractors doesn't fall on one team. It pulls in finance, HR, and operations simultaneously, with no single department holding clear ownership of the problem.

• 85% of respondents said contractor management requires help from accounting, HR, and operations teams
• 68% of teams spend 21+ hours per month on compliance-related work alone
• 60% spend 21+ hours per month on contractor support, including troubleshooting and answering questions
• 26% need between 41 and 80 hours per month just to onboard contractors
• Operations teams are more than twice as likely as any other department to exceed 81 hours per month on contractor-related work

Every hour spent chasing down W-9s, troubleshooting payment errors, or manually managing compliance is an hour not spent on work that moves the business forward. And as contractor hiring scales, so does every one of these numbers.

The high cost of doing nothing

For a mid-size contractor program spending between $1M and $2M per month, the combined cost of manual administration, contractor churn, and compliance exposure can exceed $500,000 annually, a figure that roughly doubles at the $2M+ threshold. These aren't abstract risks. They show up in delayed projects, frustrated contractors, overwhelmed operations teams, and compliance exposure that grows quietly in the background… until it doesn't.

The full picture – including what companies are doing about it and what the most operationally mature organizations look like – is in The Future of Flexible Work report. Download The Future of Flexible Work report here.

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