The Case for Technology-First Contingent Workforce Management

For full-time staff, most organizations would probably say they have pretty solid software for payroll, benefits, and compliance. It’s handled by mature systems, and everyone on the internal roster is covered. 

The tools for managing freelancers, contractors, seasonal workers, and other flexible talent, however, are often a lot thinner: e.g., a spreadsheet, a staffing agency, a payment process that only one person really understands, and so forth.  

AllWork’s CEO, Glenn Laumeister, has spent the better part of a decade closing that gap, and he recently got into the “why” of it all in a conversation with Jeff Nugent of the Contingent Workforce Institute / Contingent Workforce Strategies group. They’ve both been in this industry long enough to remember when it was a service business, and the conversation kept circling back to how far it’s moved since. Here are some of the biggest takeaways on contingent workforce management from their “Ask the Expert” session (which you can watch in its entirety here).  

A period of underinvestment

The contingent workforce has been growing steadily across every income level.  

“It’s all incomes, all job descriptions,” Glenn said, pointing to occupations like clinical researchers on multiyear contracts, network engineers, seasonal retail staff, and traveling nurses. 

However, software hasn’t kept up with this growth. Big companies already have their internal teams covered, as Glenn was quick to point out: “You’ve got Workday, you’ve got Oracle, you’ve got PeopleSoft.” But what’s missing is the equivalent for everyone else.  

When Glenn was Googling leading HCM platforms, he pulled up a list of the top 500 (and noted there are many more), but only a small number were built specifically for contingent work at all (and with several of those really sourcing marketplaces that solve a different problem). 

“There’s been a huge underinvestment in software and platforms to help companies manage this contingent workforce,” he said, “and it got to a breaking point during COVID.” 

For a long time, companies could live with this gap, with Glenn referring to it as more of an “irritant.”  

“It was painful, but it wasn’t acute until COVID,” he said. Then, companies moved a lot more of their workforce into contingent roles—and fast. A team set up to manage 50 contingent workers might suddenly be told to handle 500… but with no system, no established partners, and no real compliance plan. 

Some of that came down to cost, but Glenn said the bigger surprise was how much of it came from workers themselves. 

“The companies said, ‘I can’t find enough full-time people. I’ve got to tap into this flexible workforce, because that’s the only way I can get enough people.’ And the talent was saying, ‘I don’t want to work 40 hours a week. I want to work 15 or 20, or I only want to work for three months, and I want to go back to school.'” 

Why companies want to own their own data

Previously, if you needed flexible workers, you called a staffing agency. As Jeff put it, the field was “traditionally more service-oriented, versus technology-oriented, which was allowing customers to do it themselves.”  

That’s the shift we’re now watching play out. Technology has become the default way companies solve operational problems, but contingent work was one of the last places it reached. Now, more companies want to own their workforce data and see it live, instead of asking a provider for a report and waiting on the reply. 

“It’s no longer ‘I want to go to a staffing agency and have them help me.’ It’s ‘I want the technology,’” Glenn explained. “I might include a staffing agency for some parts of it, but I want to control the data. I want real-time visibility. I don’t want it sitting in a staffing agency’s database. I want it in my cloud.” 

Glenn compares it to booking a flight. You used to call the airline and let an agent read you seats, times, and fares. Now, you compare carriers yourself right on your phone, pick your own seat, and change plans without consulting anyone. 

“It’s much better if you give the customer visibility into the data so they can make their own decisions,” he said. “And if they need help, we’re there.” 

Jeff pointed out that the platforms companies use to manage this workforce have gotten a whole lot easier and more user-friendly, too. 

“It allows for more self-service than needing someone to call or help them onboard,” he noted. 

It cuts both ways in that managers get more direct control over hiring and budgets, and workers can onboard themselves instead of waiting for someone to key in their details by hand. 

Which companies succeed with it

Glenn described a few traits that the companies who do well with this tend to share. 

The first is that they’re data-driven. They spend enough on flexible labor that it counts as a strategic expense, and their finance teams are paying close enough attention to ask why one month costs more than the last.  

The data they need usually exists already, but the problem is that it’s scattered across files or locked inside a provider’s system they can’t query on their own.  

“It’s a strategic spend for that company. It’s enough money that it’s worth analyzing, so they want the data. But a lot of times, they have 10 service providers and they have to mash it all together,” Glenn explained. “So they’re always getting a piece of the story, not the whole story.” 

The second is that they’re comfortable with software. If a company already runs things on a handful of good platforms, you don’t typically have to sell them on why a system of record beats a spreadsheet. 

The third is that they genuinely care about the talent experience, especially where good people are hard to find. When onboarding is slow or clunky, a strong candidate can take another offer before the paperwork clears, so these companies want the process to be fast and smooth.  

Glenn told the story of a retail employer whose HR director spent her weekends adding flexible workers to a payroll system that was never meant for them, typing in names from emails by hand.  

Once the workers could onboard themselves, her verdict was short: “I got my weekends back.” 

Glenn also warned that rolling new tools out to a large, established workforce can backfire if it’s handled poorly. 

“Making a good first impression on your talent is critical. If you have a large workforce, the change management can be very difficult, going from one system to another,” he explained, adding that you should ensure the change is a “net positive for the talent.” 

The rise of SOW spend

One of the fastest-growing corners of contingent work is statement of work (SOW) spend: contractors hired directly, often outside any formal program. Jeff sees this climbing particularly fast. 

“We see a massive amount of spend happening in what we as an industry are calling SOW,” he said. “You can also call it rogue spend—if you’re so inclined—because it’s not going through the program.” 

The reason isn’t complicated, and Jeff traced it back to how managers actually work. 

“Managers aren’t here to do internal processing roles. They’re here to do a job. They’re always going to take the path of least resistance.” 

Talent, for its part, increasingly wants to work directly with the companies hiring them. The trouble starts when all that spending piles up out of view—until finance asks who signed off on it, and whether the company is even compliant in every state in which those contractors now live.  

Glenn’s argument is that a technology-first setup doesn’t fight that trend but simply organizes things, giving a company a way to track the spend, report on it, and budget against it. 

“It’ll cost them less, it’ll be more flexible and faster, and it’ll reduce those friction points with the talent.” 

That single point of ownership matters most on compliance, where responsibility tends to fall through the cracks between vendors. 

Where to start

Glenn’s main piece of advice is not to start from scratch. Search “freelancer management” or “contingent management,” he said, and you’ll mostly see companies solving some adjacent but different problem—which leaves you no clearer on what to look for.  

He suggested a more direct route: 

“I’d consult a peer group and say, here’s what I’m trying to accomplish—who should I be talking to? What are these companies even called? Get peer input. It’s very hard to do from a cold start.” 

Part of the challenge, Glenn added, is that buyers have less time than ever to sort this out: “In the old days, you’d have a two-hour discovery session. Now you might get 10 minutes.” 

Jeff’s advice was more about doing your homework before you start shopping. 

“Have your ducks in a row,” he said. “Get your data organized, and then start to evaluate the products out there.” 

He closed on the longer arc of where all this is heading: 

“We’ve spent 30 years trying to solve the problem of finding a person, matching a job, and getting them onboarded, and we’ve put a lot of layers in between,” Jeff said. “The trend now is bringing it back to an easier experience, especially if we already know the talent. Let’s get them on and working, and make it a seamless, self-driven experience, but give the enterprise the data they need to make better decisions and ensure compliance.” 

What comes next

That mix is exactly what AllWork was built to be. Plenty of companies will sell you software, and plenty will act as your employer of record (EOR) and run payroll, but as Glenn pointed out, the two rarely come from the same place (which is how organizations end up stuck in the gap wondering who’s actually responsible when something goes wrong). AllWork provides both: technology to give you real-time visibility and control over your flexible workforce, plus a full EOR. If you’ve been trying to stitch that together yourself, we’d love to show you what it looks like in one place—you can request a demo of AllWork here.