Being a contingent workforce program leader is one of the hardest jobs in a large enterprise. I don't think enough people say that out loud.
I've spent the last ten-plus years sitting across from these people. Fortune 500 companies, global programs, hundreds of millions in contingent spend. And what strikes me every single time is how much they're being asked to hold at once.
Think about it.
On the one hand, you've got hiring managers who need talent yesterday. Not next week. Yesterday. Projects are stalled, deadlines are slipping, and patience for process is low.
On the other side, you've got procurement and senior leadership who need that same talent, but within budget. Then there's compliance, with different rules by country, by state, by city, changing constantly. And finally, the talent themselves. Real people, with options, expectations, and a direct experience of how your program operates.
A contingent workforce program manager has to balance all of that, all the time. And when the program spans multiple countries?
The complexity multiplies fast.
But here’s the part that doesn’t get talked about enough: this complexity has a cost.
Every delay in hiring pushes timelines. Every workaround introduces risk. Every gap in visibility creates budget leakage. Most of it doesn’t show up cleanly in a report, but it compounds across the business every day.
And structurally, most programs are set up to force trade-offs.
Move fast, and you lose control. Lockdown compliance, and you slow the business. Reduce cost, and something else gives. The expectation is to deliver all three simultaneously, but the underlying systems weren’t designed for that reality.
We’ve normalized a level of operational friction in contingent workforce programs that wouldn’t be accepted anywhere else in the business.
So when things don’t work, people look for something to blame. The program. The suppliers. The VMS. The MSP. But most of the time, the real problem is structural. These leaders are being asked to deliver against competing priorities with a fragmented set of tools that weren’t built to work together.
That’s not a performance issue. It’s a system design issue.
The strongest leaders are the ones who’ve managed to make it work anyway. They’ve built programs that hold together despite the constraints, and they protect them carefully. They’re not looking for a revolution. They want something that fits into what they’ve built and makes it better, without adding more disruption.
And that’s where things are starting to shift.
The programs that are breaking through aren’t working harder. They’re simplifying. Reducing fragmentation. Creating clearer visibility by default. Designing for speed, cost, and compliance to coexist, rather than constantly trading off between them.
That’s what the next phase of contingent workforce management looks like.
If you run a contingent workforce program, what's the one thing you wish the business understood better about your job?
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Author
Ernesto Lamaina
GM, Lifted
Ernesto Lamaina is the General Manager of Lifted, an Upwork company dedicated to helping enterprises source, engage, and manage contingent talent across every contract type—independent contractors, staff augmentation, employer of record, and managed services.
