Why Flexible Work Needs a Better Operating Model

When AllWork’s CEO, Glenn Laumeister, recently sat down with Matt Mottola on the Human Cloud podcast, both described a shift they’ve been seeing for years: Companies are relying on flexible workers for long-term, business-critical work. What used to be handled more informally (or through multiple staffing layers) is now increasingly tied directly to core operations.  

Let’s dive into their discussion on how organizations are managing flexible teams today, why visibility has become a priority, and where legacy systems continue to create friction. 

Flexible work is now long-term and manager-led

Glenn noted that many of the challenges enterprises face today resemble the friction he experienced years ago when hiring freelancers for his own tech companies. Basically, engagements felt manual and disconnected from the systems used for full-time employees. 

“Every time I did it, it was messy and full of friction,” he said. 

And those same issues now appear in much larger organizations, but the difference is that the work is more strategic, and the stakes are higher. Many flexible workers stay on projects for six, 12, or even 24 months; they function as core contributors, rather than short-term contractors. 

Matt added that as teams become more distributed, economic pressure has pushed companies to reassess how they use flexible talent. The model is expanding quickly, but the infrastructure supporting it hasn’t kept up. 

Why staffing layers don’t support modern flexible teams

A big theme throughout the conversation was the disconnect between managers and the workers they rely on. 

Glenn described how legacy staffing models—MSPs, VMSes, and multi-layer processes—often create distance between the manager requesting work and the person doing it. 

And when work is long-term and high-skill, that distance then becomes a real problem. After all, managers want visibility and direct communication, especially when flexible workers are tied to important business outcomes. 

Matt summarized the point clearly: AllWork functions as “the invisible infrastructure for the visible worker.” Rather than adding another layer, it supports the relationship between managers and their flexible teams. 

For Glenn, that relationship is what determines the success of a contingent or flexible program. 

The compliance and classification challenges companies are facing

Compliance has also moved more to the forefront as flexible work becomes more distributed. In turn, many HR teams now manage workers in states where the company has never operated. 

Glenn noted how often he sees this, when HR leaders regularly ask how to pay and classify workers correctly when they suddenly have talent spread across multiple states. 

Older approaches, like paying independent workers informally or handling taxes manually, no longer work. Glenn recalled a marketplace paying $5 million per quarter through PayPal with no compliance structure. 

“It worked until it didn’t,” he said. 

As the flexible workforce has grown and professionalized, compliance and classification have become foundational rather than optional. 

When enterprise systems can’t support flexible work

Glenn shared a clear example of this gap: A global luxury brand tried to run thousands of flexible workers through its enterprise payroll platform, but the system wasn’t designed for variable schedules or real-time changes. Managers emailed personal information to HR, and HR staff spent weekends manually entering it. 

Switching to AllWork gave the company what its full-time systems couldn’t: e.g., managers gained visibility, compliance became part of the workflow, and manual work that had built up over years magically disappeared. 

As Glenn explained, an HR leader summed up the difference simply by telling him, “I have my weekends back!” 

Why ‘temp to hire’ doesn’t match today’s independent workforce

Matt pointed out another shift: The assumption that contractors want full-time roles is outdated. 

Many high-skill independent workers choose flexibility intentionally. Glenn noted that conversions to full-time roles have been declining in higher-skill segments for years. 

Many independent workers stay flexible long term, and companies are increasingly structured around that reality. This challenges older staffing models built on short rotations and temp-to-perm pipelines. 

Structure, flexibility, and clear visibility

Flexible work has become part of everyday operations, not a short-term add-on. That shift puts more pressure on the systems companies use to manage it. When teams rely on outdated layers or tools designed for full-time employees, managers lose visibility, and HR carries unnecessary manual work.

The conversation on the Human Cloud underscored how common these issues are. Companies are looking for operating models that support long-term independent workers, handle compliance consistently, and give managers a clear view of who is working. The goal isn’t more complexity. It’s a structure that matches how work actually happens today.

To hear the full discussion, listen to the episode on the Human Cloud podcast.