Insights on the world of work | Insights on the world of work

Forget climbing the corporate ladder. In the age of artificial intelligence, the ladder itself is being dismantled and rebuilt into something entirely new. According to John Winsor, a leading voice on the future of work and an Executive Fellow at Harvard Business School, we’re on the edge of a shift that will redefine not just how we work—but what a “job” even is.

John Winsor Founder/Chairman
Open Assembly

“The tasks will probably stay the same,” Winsor said on the Workforce Observer podcast, “but will they go toward the same jobs?”

We’re moving away from rigid job descriptions and into an open-talent world where your skills matter far more than your title.

To explain this, Winsor points to the shipping container—what author Sangeet Paul Choudary calls a simple innovation that reorganized an entire system. AI is doing the same thing to our careers. Take the typist: once a specialized role because mistakes were costly, the job didn’t disappear with the rise of word processors. The work simply spread to everyone. A once-central function became decentralized.

The Role of Staffing Firms as Transformation Partners

As AI breaks down old corporate silos, staffing industry insiders see a rare opening. With a panoramic view of talent and skills across the market, staffing firms can spot gaps early and recognize what “AI-ready” really looks like. They can help companies:

Design targeted training.
Bring in expert contractors.
Build flexible pipelines.

In this new world, they’re no longer just recruiters—they're transformation partners.

The Rise of the "Portfolio Career"

This shift also paves the way for what Winsor calls the “portfolio career.” Instead of a linear climb, more people will become micro-entrepreneurs, stitching together projects and clients. It offers huge freedom, but also challenges—especially in countries like the U.S., where benefits are tightly tied to traditional employment.

Mindset Shift: Tool vs. Teammate

One of Winsor’s biggest insights is about our mindset.

“What’s the difference between thinking about AI as a tool versus a teammate?”

His research at Harvard’s Digital Data and Design Institute shows that when people treat AI like a collaborator—even giving it a name—it leads to better integration and more creativity. This “cybernetic teammate” isn’t here to replace us. It’s here to take on executional tasks so humans can focus on what we uniquely do best: judgment, taste, integration, and trust.

Navigating the Future: A Call for Curiosity and Courage

So how do we prepare for what’s coming?

For Leaders: Winsor stresses deep engagement. The C-suite can’t sit this one out—they have to champion the shift. Building a center of excellence to test and evaluate AI tools can make experimentation safe and strategic.

For Individuals: The mandate is simple: stay curious, keep learning, and keep moving. In a world where skills evolve constantly, adaptability becomes the ultimate job security. As Winsor puts it:

“If you just want to call it in and do a job and not be that into it, you’re not going to have a job. It’s just not going to happen.”

The transition may be bumpy, but the upside is enormous. By embracing open-talent models, treating AI as a collaborator, and cultivating a culture of continuous learning, we can build a future of work that’s more dynamic, more innovative, and—ironically—more human.