The Fastest-Growing Companies Don't Manage Contractors Like Everyone Else

The tools most companies use to manage contractors were built for a different era of work. Payroll platforms were designed to pay employees. Vendor management systems were designed to handle suppliers. Neither was built for the contractor. This type of worker -- already performing billable, mission-critical work for businesses -- requires a fundamentally different set of workflows, payment structures, and compliance processes.

Wingspan and Global Surveyz surveyed 500+ HR and finance leaders to understand more about what independent contracting looks like in 2026 and beyond. Below are key findings from the report related to how companies feel about their current contractor management solutions, and their plans for the future. For all the insights – including findings related to managing contractors at scale – download The Future of Flexible Work report.

Satisfaction with current solutions is lukewarm at best

Most companies know their contractor management infrastructure isn't working as well as it should. The survey data makes that clear:

• Only 59% of respondents describe themselves as mildly satisfied with their current contractor management solutions
• Just 18% say they are very satisfied with their current processes
• 95% of companies use three or more tools to manage the contractor lifecycle, a fragmentation that creates complexity without delivering results
• Among companies spending $1M or more on contractors, half rely on seven or more tools, more than three times the rate of lower-spend companies

The tools in use today were largely not built for contractor onboarding and payments at scale. They were initially designed to support employees or vendors, and were serviceable in a bygone era, one where contractors were occasional hires rather than core contributors driving billable revenue. As a result, contractor functionality was added as an afterthought. The gap between what companies need and what their current tools can deliver is widening. That mismatch becomes increasingly costly as contractor headcount grows.

The market is (slowly) moving in a new direction

Despite widespread dissatisfaction, investment in purpose-built contractor management solutions has been slow to follow. That is beginning to change:

• Only 35% of companies have already invested in a system built specifically for contractor onboarding, pay, and tax workflows
• 60% of respondents are either planning to invest or actively evaluating purpose-built options

Companies not yet considering an upgrade are opening themselves up to revenue risk, ceding ground to competitors already positioning themselves to attract and retain contractors more effectively.

Why modern contractor management systems are a competitive advantage

The companies investing in purpose-built contractor management are building a structural advantage in the competition for skilled contractor talent. Here’s why:

1. Faster onboarding means faster revenue – Every day a contractor spends navigating a slow, confusing onboarding process is a day they can’t deliver billable work.
2. Payment speed drives retention – Companies paying contractors faster and more transparently will likely see higher retention rates; 96% of providers on Octave Therapy are repeat payees after switching to Wingspan.
3. Compliance automation reduces exposure – Avoiding a single misclassification penalty can save upwards of $50,000 in combined penalties, back taxes, and interest – and that’s before legal fees, a figure that compounds across a large contractor program.
4. Centralized systems frees up time across departments – Consolidating contractor management into a single platform removes the fragmentation that is currently consuming hundreds of hours per month across finance, HR and operations.

The window is open for change

Fifty-six percent of companies are planning to scale their contractor workforce over the next three years. The ones building the right infrastructure now will be the ones able to do that without the operational drag currently holding most of their competitors back. As Greg Franczyk, co-founder and CTO of Wingspan, puts it: companies that can't onboard and pay contractors efficiently will fall behind. Every time a product team wants to build something new, they'll be slowed down by infrastructure that wasn't built for this use case.

The Future of Flexible Work report covers the full picture of contractor management – from the operational burden of managing contractors at scale, to the payment and onboarding issues driving contractor dissatisfaction, to what the most forward-thinking companies are doing differently.

Download The Future of Flexible Work report here.