The rise of the independent contractor is a structural shift in how work gets done, and the professionals powering some of today's fastest-growing companies aren't on payroll. They're contractors, freelancers, and independent specialists who are choosing who they work with, when they work, and increasingly, how much they earn.
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 use this group of highly qualified freelancers. For all the insights – including findings related to managing contractors at scale – download The Future of Flexible Work report.
Contractors are core contributors
The gig worker stereotype is overdue for retirement. According to our survey data, the majority of companies have moved well beyond using contractors for one-off projects or seasonal gaps.
- 83% of companies treat contractors as core contributors rather than purely temporary staff
- 41% describe their contractor workforce as mostly or entirely highly skilled professionals
- 80%+ of these contractors are delivering billable work or services to a large or moderate extent
The contractors showing up in these numbers are the same people driving revenue, delivering client work, and filling specialized roles that full-time hiring simply can't keep pace with.
These are not small contractor programs
One of the clearest signals that contractor work has become a core business function is the sheer scale at which companies are engaging these workers. These are substantial, complex contractor programs that require real infrastructure to manage.
- 36% of companies we surveyed work with between 200-499 contractors in a given year – the single largest group in our survey
- 24% manage between 500-999 contractors annually
- 12% are running programs of 1000-4999 contractors
- Nearly 4% are managing between 5000+ contractors in a given year
When you combine the scale of these programs with the fact that 83% of respondents say contractors are delivering billable work, the operational stakes become clear. A contractor program of 500 or more people – with payments, compliance, onboarding, and support to manage across all of them – is not a back-office function.
The relationships contractors have with companies last longer than you think
Backing up these findings are Wingspan's own platform data, which tells a story about contractor engagement that cuts against the conventional wisdom of short-term, transactional work.
- Contractors receive an average of 18 payments over the course of their engagement
- The average contractor stays active for nearly 11 months
- The median engagement runs 8 months, suggesting that even typical contractor relationships are sustained and recurring
Gig workers pick up a single project and move on. Professional contractors build ongoing relationships with the companies they work with – and in many cases, move fluidly between contracting and full-time roles as business needs evolve.
Companies are doubling down on contractor hiring
The demand for flexible, highly skilled labor isn't slowing down. Our survey found that companies are hiring contractors for increasingly strategic reasons:
- 71% hire contractors to scale teams up or down quickly
- 44% cite specialized expertise
- 43% point to project-based work needs
- 56% of companies plan to hire more professional contractors in the next three years
This lines up with broader market data. MBO Partners' 2025 State of Independence report found that the number of high-earning independents – those making over $100,000 annually – has nearly doubled since 2020 to 5.6 million professionals. The talent pool is growing, and companies are taking advantage.
What this means for your business
Sure, the businesses winning the contractor talent war offer competitive rates. But that’s table stakes. The companies attracting the most sought after talent offer contractors a better experience – faster onboarding, clearer communication, and payments that arrive on time. For the businesses still treating contractors as an afterthought, the gap between them and their competitors is widening.
The data on contractor hiring is just the beginning. The Future of Flexible Work report covers the full picture – 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.
