The Future of Flexible Work: Why the Contractor Experience Matters

Missed the webinar? Watch the recording, or read the recap below.

The Future of Flexible Work: Why the Contractor Experience Matters — Key Takeaways

Ask any finance, HR, or operations leader about their biggest workforce challenge right now, and chances are it comes down to one thing: contractors. Not managing them in theory — managing them in practice, at scale, across fragmented tools, with no single owner and no purpose-built system to hold it all together.

That's exactly what we unpacked in our recent webinar with Don Weinstein, ADP's former Chief Product & Technology Officer, and Greg Franczyk, Wingspan's Co-Founder & CTO. We surveyed 500+ HR, Finance, and Operations leaders to understand the real state of contractor management in 2026 — and the findings were striking. Watch the recording here, or read on for our key takeaways.

Finding 1: Contractors are now core contributors — not an afterthought

The old mental model of a contractor — someone you bring in for a short, defined project and then let go — is almost completely out of date. On Wingspan's own platform, the average contractor engagement runs close to a year and involves around 18 separate payments. Contractors have stopped being a staffing supplement. They're part of how businesses run week to week.

84% of companies now use contractors for work once exclusively reserved for full-time employees, and 56% plan to hire more in the next three years. As Greg put it: "Contractor has stopped describing the duration of the relationship. It's really started describing the structure of it."

And yet, most companies are still managing this growing workforce with systems that were never designed for them.

Finding 2: The hidden friction of contractor management creates a growing operational burden

When a company spends money, it goes one of two places: employees or vendors. Independent contractors fit neither bucket cleanly — and that's where the dysfunction begins. 95% of companies use 3 or more tools to manage their contractor lifecycle (with some using 7+), each one a point solution filling a specific gap. The same contractor exists as seven different records across seven different systems, with no shared primary key tying them together.

Operations teams are twice as likely as any other department to spend 81+ hours per month on contractor-related work. And 73% of CFOs feel very confident in how they're managing contractors — while only 14% of Directors share that confidence.

Don explained why this happens: "There is no overarching organizational ownership in most companies. Contractors don't have a home. And as a result, it just shouldn't be a surprise that there is no process, no system, no workflow — because there was historically no design point."

Finding 3: Contractor satisfaction hinges on payment speed and clear communication

Contractors are expected to deliver work like an employee but be paid like a vendor — often waiting 30 to 60 days after invoice submission. In a world where 75% of the traditional workforce gets paid biweekly or faster, and consumer payment tools like Venmo and Zelle have set a new expectation for instant money movement, the Net-30 model is no longer sustainable.

66% of contractors cite slow or untimely payments as their #1 complaint. 53% point to payment reconciliation delays. And 43% of companies can't give contractors clear visibility into where they stand in the onboarding process.

As Don put it: "Why would we think that the same trends that permeate the traditional employment world and the consumer world don't apply to contractors? It makes no sense."

Good onboarding, Greg explained, comes down to three things: a clear list of what needs to be done, a single place where that list lives, and a process that feels natural to move through. A bad onboarding is 10 emails from 10 different vendors asking for bits and pieces of information, with no single place a contractor can go to see what's missing.

Finding 4: Purpose-built contractor management systems are now a competitive advantage

Only 35% of companies have invested in a purpose-built contractor management system — but 60% are planning to or actively evaluating. The companies pulling ahead aren't just hiring more contractors. They're investing in systems built specifically for the contractor lifecycle: onboarding, payments, compliance, and tax — managed in one place, not stitched together across a web of disconnected tools.

Don's three-step framework for jumpstarting contractor management:

1. Get your arms around the data. Most companies know their employee headcount off the top of their head. But how many contractors do you have right now? Where are they? What are they working on? Start there.
2. Give contractors a designated organizational owner. While it could be your HR, Finance, or Operations leader, Don recommends HR owns it as part of the overall people experience.
3. Build a process and implement a system. Once you have visibility and ownership in place, you can design a contractor experience worth having — and invest in the technology to automate it.

And as Don summarized the moment we're in: "Revolutions happen slowly, gradually, and then suddenly. We're seeing the suddenly right now."

Ready to put this framework into practice?

Learn more about how Wingspan can help you modernize your contractor management stack — from onboarding to payments to compliance — in one purpose-built platform. → Book a demo

Download the Future of Flexible Work Report

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. Read the report here: