2026 Report

The Future of Flexible Work Report

New data from 500+ Finance, HR, and Operations leaders shows how contractors are reshaping the workforce, and where most companies still have a gap to close.

Wingspan Survey of 500+ leaders
84%

of businesses say contractors now do work once reserved for employees.

Highly skilled contractors are doing core, billable work.

What's inside

  • 01 How independent contractors became a fundamental part of the modern workforce.
  • 02 Where contractor management quietly creates a growing operational burden.
  • 03 Why contractor experience now decides who keeps the best talent.
Respondents
500+ Finance, HR & Operations leaders
Company size
200–4,999 employees
Source
Wingspan × Global Surveyz, 2026

Who this is for

Built for the teams that run contractor operations.

Managing contractors is spread across Finance, HR, and Operations at once. That is exactly why most leadership teams underestimate its true cost. This report is for the people who own the work.

Operations

Onboarding, capacity planning, contractor support, and experience at scale.

Finance

Payments, reconciliation, spend visibility, and 1099 readiness.

HR & talent

Classification, onboarding, documentation, and retention.

Executive leaders

Closing the visibility gap between the C-suite and the teams doing the work.

Key findings

Contractors are now core contributors

The gig economy narrative has long overshadowed a bigger shift in the workforce. Highly skilled independent contractors do more than fill gaps. They drive revenue.

Independent contractors, particularly in healthcare, professional services, and insurance, are core contributors. They deliver billable work and specialized expertise that companies can't hire fast enough. With 56% of companies planning to grow their contractor workforce in the next three years, the infrastructure you choose today decides whether that growth runs smoothly or stalls.

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 the data.

Operations teams are twice as likely as any other department to exceed 81 hours per month on contractor-related work. Because the burden is spread across Finance, HR, and Operations at once, most leadership teams underestimate the true cost to the business.

Contractor retention hinges on payment speed and a clear onboarding experience

High-demand contractors can choose who they work with. For them, payment delays and onboarding confusion are dealbreakers. Since 84% of contractors do billable work, churn is a direct threat to revenue.

Speed and timeliness of payments is the #1 contractor complaint (66%), followed by payment-reconciliation delays (53%) and a lack of payment transparency (46%). On the company side, integration with internal workflows (54%) and compliance and classification (52%) top the list. That friction compounds at every stage of the contractor lifecycle.

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

Get the report

Download the Future of Flexible Work Report.

Get the full breakdown of how contractors are reshaping the workforce, where the operational burden is hiding, and what the highest-performing teams are doing differently. We’ll email you the report.

Inside the report

The numbers behind the contractor shift.

Benchmarks from 500+ Finance, HR, and Operations leaders on how contractors are hired, paid, and managed today.

84%

say contractors now do work once reserved for employees.

83% already treat contractors as core contributors.

66%

name payment speed as their #1 contractor complaint.

The top driver of contractor churn.

18%

are very satisfied with their current contractor process.

Even though 95% already juggle three or more tools.

The takeaway

Companies that win in a contractor-first world are the ones investing now in purpose-built infrastructure to support it.

Download the full report:

Read our full Privacy Policy to learn more about your rights and our data retention practices.

Webinar titled 'The Future of Flexible Work: Why the Contractor Experience Matters' featuring Don Weinstein, Greg Franczyk, and Sara Strope from Wingspan.

Webinar recording

Want more on the key findings from The Future of Flexible Work: Why the Contractor Experience Matters? Watch the on-demand recording.

Watch the recording