As part of a recent Staffing Industry Analysts (SIA) webinar, AllWork CEO Glenn Laumeister joined Dustin Talley, Founder of Direct Collective, to share what they’re seeing as more companies expand their contingent workforce programs.
The conversation centered on what it takes to bring order, visibility, and connection to a workforce that’s more flexible (and more complex!) than ever.
“It’s getting harder, not easier, to manage the contingent workforce,” Glenn said. “And yet there’s never been a time when it’s more important.”
The growing mix of worker types
Many teams now manage a mix of employees, freelancers, contractors, and shift workers, each with their own rules, systems, compliance requirements, and so forth.
“The workforce is becoming more diverse and complex,” Glenn said. “We have all these different work classifications, changing labor laws, and the rise of gig work.”
And that complexity spreads across departments, too: e.g., HR handles classification and paperwork, operations juggles scheduling, and finance tracks costs and headcount across multiple systems.
The result is extra work for everyone and, unfortunately, limited visibility into what’s actually happening.
Outdated systems, modern workflows
Many of the tools companies use today were built for a different kind of workforce: one that assumed everyone was full time and on payroll. Glenn described what that looks like in practice.
“Every time I hired a consultant or freelancer, it was a different process—lots of manual steps, lots of work-arounds, no workflows designed for this labor force.”
Even well-intentioned systems can end up creating more work. Companies add new tools to fill gaps, and over time, those fixes start to overlap. What should be one workflow turns into three or four, Glenn explained.
Too many tools
Out in the field, Dustin has seen his fair share of this up close. With nearly two decades in contingent workforce management, he’s watched even the most mature programs wrestle with disconnected systems.
“It’s a fragmented ecosystem,” he said. “Even 20 or 30 years into some programs, they’re still fragmented.”
He noted that some organizations run as many as nine tools across one program. Each new system means another source of data to reconcile—and, in turn, more opportunities for errors.
“If we don’t give teams the right tools, they’ll create their own,” Dustin said. “That’s when data gets lost and compliance risk creeps in.”
He also pointed out that most legacy systems weren’t initially designed for the people who actually use them nowadays.
“A lot of systems were designed for MSPs or suppliers,” he said. “The people on both ends of the process—the managers and the talent—weren’t the ones these systems were built for.”
Compliance that can’t fall behind
Compliance remains one of the hardest things to manage across multiple tools and worker types. Regulations change quickly, but updates often lag.
“Customers might have a system, but there’s no one to call when it doesn’t work or when laws change,” Glenn said. “You can’t separate software from compliance. It has to be built in from onboarding through termination.”
He mentioned that while laws like California’s meal and rest break rules can shift often, companies that rely on third-party software to stay compliant are taking on unnecessary risk.
“We at AllWork maintain a database of those new laws and update them immediately if anything changes,” he said. “It’s not easy, but it has to stay current.”
Dustin added that maintenance is where even good tools fall short: “The setup phase might look great. Then, two years later, the tool starts to look outdated—UI, compliance, everything. Maintaining it is the hard part.”
The view from the front line
In the end, there’s a lot of friction that lands on managers who just want to get someone working quickly.
“A hiring manager might know exactly who they want to work with but can’t figure out how to get them started,” Dustin said. “It’s confusing for everyone.”
Visibility helps close that gap.
“We built AllWork so managers can see if someone’s ready to work or not,” Glenn said. “If they’re not, it shows exactly what’s missing—like a document or verification step—so they can fix it fast.”
Even simple improvements in onboarding visibility can reduce delays and keep pre-identified talent engaged instead of waiting in limbo.
Better visibility, fewer surprises
When programs scale across different teams or regions, visibility becomes one of the hardest things to maintain for organizations.
“People used to export everything into Excel and run reports 60 days later,” Glenn said. “By then, the money was already spent.”
That lag makes it hard for managers to adjust budgets or schedules in time. On the other hand, having real-time data lets managers see what’s happening as it happens.
Dustin compared it to something like buying a new pair of kicks online: “When I order a pair of shoes, I can see where they are in real time. Managers want that same visibility into where their talent is in the process.”
Being able to see progress live—not after the fact—reduces manual work and helps keep everyone aligned.
What AI can (and can’t) do in flexible work
Artificial intelligence came up as part of the discussion, but in a practical sense, not as a buzzword. Glenn shared how predictive scheduling, for example, can help identify the right worker for a shift based on performance and availability. It saves time for managers while matching qualified talent to the right opportunities.
He also talked about short post-shift surveys that collect feedback directly from workers.
“We can ask questions about how their day went, if they had what they needed, or if something slowed them down,” he explained. “That data can help managers see what’s really happening on the ground.”
Dustin added that most program leaders aren’t building AI tools themselves, but they’re eager for technology partners to make it more “useful.”
“They’re not the ones implementing it,” he said. “They look to providers to bring them something practical. It’s early, but everyone wants it to actually solve a problem.”
People still matter, of course
Technology can simplify a lot, but it can’t replace support. Managers still need real people to help when programs change or problems surface, Glenn and Dustin emphasized.
“You can buy a system, but if there’s no one to call when it doesn’t work, it won’t deliver the value you expect,” Glenn noted. “You need people behind the system who can help.”
That balance—modern tools supported by responsive teams—is what enables programs to grow without losing connection to the people running them.
The bottom line
Managing a contingent workforce will always be complex, but it certainly doesn’t have to be chaotic. While companies want fewer systems, better visibility, and tools that stay current as regulations evolve, workers want faster onboarding and clearer communication. And the solutions that last are the ones that make those connections easier for both sides.
As Dustin put it, “We’re all just trying to give managers and workers a better experience.”
For more on how AllWork brings clarity to the chaos of contingent work, explore our solutions here.