The Future of Flexible Work: 2026 report
We surveyed 500+ U.S. finance, HR, and operations leaders about how their companies hire, pay, and manage independent contractors. Here are the key findings and how we ran the survey.
By Wingspan with Global Surveyz. Survey fielded February to March 2026.
Key findings
All figures come from Wingspan's survey of 500+ U.S. finance, HR, and operations leaders, fielded February to March 2026, unless noted.
1. Contractors now do core, billable work
Most companies in the survey rely on contractors for regular, revenue-producing work. Wingspan platform data shows the average contractor engagement runs nearly a year and includes an average of 18 payments.
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84% say contractors now do work once reserved for employees.
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83% treat contractors as core contributors.
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56% plan to hire more professional contractors in the next three years.
In the full report: How many contractors companies hire and pay each month, why they hire them, and how the mix differs by industry.
See how the Wingspan platform works and the industries Wingspan serves.
2. Contractor work is spread across teams, so leaders underestimate it
No single team carries the full load, which makes the total cost hard to see from the top of the org chart.
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85% say managing contractors takes help from accounting, HR, and operations teams.
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73% of CFOs feel very confident in how their company manages contractors, while just 14% of Directors say the same.
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95% use three or more tools to manage the contractor lifecycle, and only 18% are very satisfied with their current process.
In the full report: Monthly hours spent on compliance, onboarding, and contractor support, and where executives and managers disagree.
See how Wingspan handles work and approvals, tax and 1099 compliance, and worker support.
3. Payment speed and onboarding decide whether contractors stay
Skilled contractors can choose who they work for. Because most contractors in this survey do billable work, losing one can cost revenue.
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66% say payment speed and timeliness is the top complaint they hear from contractors.
In the full report: The other complaints contractors raise, the biggest challenges companies face, how payment timing gets harder as companies grow, and where onboarding breaks down.
See how Wingspan onboards and verifies workers and handles worker payments.
4. Most companies are rethinking their contractor systems
Satisfaction with current tools is low, and most companies are looking at alternatives.
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35% have invested in a system built for contractor onboarding, pay, and tax. Another 60% are planning to invest or evaluating options.
In the full report: What teams can do now, with results from Teladoc, CRU Group, and Fizz Social.
See the full platform, how Wingspan compares, or what you could save by switching.
Download the full report
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Methodology
Wingspan ran this survey with research firm Global Surveyz. Global Surveyz collected and analyzed the data on Wingspan's behalf.
| Item | Detail |
|---|---|
| Respondents | 500+ |
| Who responded | Full-time employees in finance, HR, or operations at the manager level or above |
| Location | United States |
| Field dates | February to March 2026 |
| Contractor volume | Companies that hire 50 to 10,000 contractors a year |
| Method | Online survey. All answers are self-reported. |
| Rounding | Percentages are rounded to the nearest whole number or one decimal place, so some totals don't add to 100%. |
Two figures on this page come from Wingspan platform data, not the survey: average engagement length and average payments per engagement. That data is anonymized and aggregated across Wingspan's customer base as of April 2026.
Who responded
| Department | Share |
|---|---|
| Operations | 44% |
| Finance | 35% |
| HR | 20% |
| Job level | Share |
|---|---|
| C-level | 24% |
| VP | 11% |
| Director | 28% |
| Head of department or function | 22% |
| Manager | 6% |
| Team lead | 3% |
| Individual contributor | 3% |
| Industry | Share |
|---|---|
| Customer support services | 26% |
| Healthcare | 14% |
| Real estate | 14% |
| Transportation and logistics | 13% |
| Marketing services | 11% |
| Professional services (law, consulting, and similar) | 10% |
| Insurance | 9% |
| Company size | Share |
|---|---|
| 1,000 to 4,999 employees | 37% |
| 500 to 999 employees | 40% |
| 200 to 499 employees | 14% |
| 50 to 199 employees | 7% |
Terms used in this survey
These definitions describe the survey as it was fielded in February and March 2026.
- Purpose-built contractor management system:
- a system built specifically for contractor onboarding, pay, and tax workflows, as opposed to employee payroll software or a set of separate tools.
- Contractor lifecycle:
- the steps from onboarding through payments, compliance tracking, document signing, and tax reporting.
- Platform data:
- anonymized, aggregated activity across Wingspan's customer base as of April 2026. It is separate from the survey.
Limitations
- Answers are self-reported. Figures reflect respondents' views and estimates, not audited records.
- Contractor complaints are secondhand. We surveyed companies, not contractors. Complaint figures show what respondents say they hear from contractors.
- Scope is U.S. companies. Results may not apply to companies outside the U.S.
- Sponsor. Wingspan produced this research and sells software for managing a flexible workforce.
- Platform data covers Wingspan customers only. Their contractor programs may differ from the wider market.
How to cite this research
Wingspan. The Future of Flexible Work: Contractor Hiring and Management Trends. 2026. Survey of 500+ U.S. finance, HR, and operations leaders, conducted with Global Surveyz, February to March 2026.
For press inquiries, data requests, or more information about this report, contact us.
Sources
- Wingspan and Global Surveyz, Future of Flexible Work survey, 500+ U.S. respondents, February to March 2026.
- Wingspan platform data, anonymized and aggregated, as of April 2026.
Reports by industry
Each industry report breaks down onboarding, payment, compliance, and support data for one industry that relies on a flexible workforce.
Watch the webinar
Our team walks through the findings with special guest Don Weinstein, ADP's former Chief Product and Technology Officer. Hear what the data means for the contractor experience in the on-demand recording.
Watch the recording