Why Contractors Are Frustrated With the Companies They Work for (and Why It Matters)

Contractors can choose who they work with. And increasingly, the quality of the payment experience – not just the rate – is what determines whether they come back. As companies scale their contractor hiring, it becomes important to understand what contractors are most dissatisfied with, where companies are falling short, and what the operational reality looks like on both sides of the relationship. The cost of that failure is showing up in churn, friction, and lost talent.

Wingspan and Global Surveyz surveyed 500+ HR and finance leaders to understand more about what managing contractors looks like in 2026 and beyond. Below are key insights from the report related to the friction in the contractor management relationship – both from the company and the contractor’s perspective. For all the report’s takeaways – including findings related to contractor hiring trends – download the full The Future of Flexible Work report.

Payment problems are the number one contractor complaint

Payments are the top contractor complaint by a wide margin, but there’s plenty more they’re frustrated with:

• 66% of respondents cited speed and timeliness of payments as the top contractor complaint
• 53% pointed to payment reconciliation delays as a significant source of friction
• 46% flagged a lack of payment transparency or communication as a problem
• 32% cited invoicing complexity as a recurring issue
• 83% of these contractors are delivering billable work, making payment dissatisfaction a direct business risk, not just an HR concern

For companies whose contractors are delivering client-facing, revenue-generating work, slow or opaque payments can affect retention – and that can directly impact the bottom line. Contractors working across multiple platforms will gravitate toward the ones that pay consistently, clearly, and on time.

Onboarding friction starts the relationship on the wrong foot

Payment issues get the most attention, but contractor dissatisfaction often begins before the first invoice is even submitted. The onboarding process is a consistent source of friction, though the specific bottlenecks vary depending on the industry.

• 54% of companies cite background checks as a key onboarding challenge
• 48% point to banking and payment setup as a significant hurdle
• 47% cite contract and NDA e-signing as a problem area
• 43% of companies say contractors struggle to understand their onboarding status
• 78% of healthcare companies cite industry license verification as their biggest onboarding headache
• 86% of Professional Services companies cite contract and NDA signing as their primary friction point

With nearly half of companies unable to give contractors clear visibility into where they stand in the process, slow or confusing onboarding risks damaging the relationship before the work even begins. BELAY, a virtual staffing company, once had an onboarding process so siloed it took contractors an average of one month to complete, a timeline that is simply not competitive in a market where skilled professionals have options.

Companies are feeling the pain too

The friction cuts both ways. Companies are struggling to both satisfy contractors and manage the operational complexity of payments and onboarding from their own side.

• 42% of companies say payment management is a top operational challenge
• 52% cite compliance and classification issues as a significant problem
• 54% point to integration with internal workflows as a major source of friction
• Teams are spending 21+ hours per month on compliance, support, and onboarding simultaneously

The source of a company’s biggest operational headache often depends on their industry: telehealth companies, for example, face payment complications tied to confirming visits and locked clinical notes before payments can be processed. Ultimately, companies that fix these issues make contractors happier and remove a source of operational drag that’s consuming hundreds of hours of team time every month (data we dive deeper into in the full report).

What the data points to

For contractors who can work with anyone, the quality of the payment experience is often what determines whether they come back. And with a majority of contractors now delivering billable work, their retention is a priority. Every bottleneck in the payment or onboarding process is a compounding risk: it costs time internally, frustrates contractors externally, and makes it harder to scale the contractor programs that companies are increasingly depending on to grow.

The full breakdown of contractor satisfaction data – including what companies are doing to address these gaps – can be found by downloading The Future of Flexible Work report.