[New Report] 500+ leaders share contractor hiring and payments trends. Get the insights.

The Future of Flexible Work Report

Contractor Management & Hiring Trends

Cover of Wingspan 2026 report titled The Future of Flexible Work with data from 500+ Finance, HR, and Operations leaders.

New data from 500+ Finance, HR & Operations leaders reveals how contractors are reshaping the workforce — and the operational gap most companies are failing to close.

  • How independent contractors are now a fundamental part of a company’s workforce.
  • Where the hidden friction of contractor management creates growing operational burdens.
  • Why contractor experience matters more than you think.
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Text highlighting over 500 US-based leaders across industries such as healthcare, insurance, customer support, and professional services, with roles in finance, HR, and operations, ranging from manager to C-Suite seniority.

Contractors are now core contributors

The gig economy narrative has long overshadowed a more significant shift in the workforce. Highly skilled independent contractors aren't filling gaps — they're driving revenue.

This is no longer gig work. Independent contractors — particularly in healthcare, professional services, and insurance — are core contributors delivering billable work and specialized expertise that companies can't hire fast enough. With 56% of companies planning to scale their contractor workforce in the next three years, the infrastructure decisions made today will determine whether that growth is smooth or a bottleneck.

Chart showing 56% of surveyed companies plan to hire more professional contractors in the next 3 years. Chart showing 73% of CFOs feel very confident in contractor management while only 14% of Directors share that confidence.

Finance, HR, and Operations view contractor management differently

When contractor management breaks down, it rarely surfaces at the top of the org chart — it gets absorbed by the Directors and Managers closest to the work. That gap between executive confidence and ground-level reality is one of the most striking findings in our data.

Operations teams are twice as likely as any other department to exceed 81 hours per month on contractor-related work. And because this burden is spread across Finance, HR, and Operations simultaneously, most leadership teams are underestimating the true cost to the business.

Contractor retention hinges on payment speed and a clear onboarding experience

For high-demand contractors who can choose who they work with, payment delays and onboarding confusion aren't just inconveniences — they're dealbreakers. And because 84% of contractors are doing billable work, churn is a direct threat to the bottom line.

This is no longer gig work. Independent contractors — particularly in healthcare, professional services, and software development — are core contributors delivering billable work and specialized expertise that companies can't hire fast enough. With 56% of companies planning to scale their contractor workforce in the next three years, the infrastructure decisions made today will determine whether that growth is smooth or a bottleneck.

Chart comparing top company complaints (42% payment management, 52% compliance/classification, 54% integration with internal workflows) and top contractor complaints (66% speed and timeliness, 53% payment reconciliation).
Webinar announcement titled 'The Future of Flexible Work: Why the Contractor Experience Matters' featuring Don Weinstein, Greg Franczyk, and Sara Strope from Wingspan.

Live Webinar

Want to learn more about the four key findings from The Future of Flexible Work: Why the Contractor Experience Matters? Join our live session on April 22 at 1:00 PM (ET).

Register here