Upwork Launches Lifted: Reinvention or Repositioning?

On August 19, 2025, Upwork Inc. unveiled Lifted, a wholly owned subsidiary aimed at servicing enterprise customers with a comprehensive suite of contingent workforce solutions.  This signals a strategic shift from selling enterprise offerings within its broader marketplace to segregating them into a dedicated business unit.

On one hand, it’s encouraging.  They’ve signaled they’re not walking away from enterprise, but rather recognizing the need to package solutions differently.

On the other, the move may be more reflective of shareholder optics than mission-aligned transformation. After repeated strategic pivots, one wonders whether this is positioning Lifted as a cleaner, enterprise-ready asset that’s ripe for acquisition, rather than truly doubling down on client-centric innovation.

Flexible Workforce Trends Amid Global Economic Uncertainty

The move comes amid growing global adoption of flexible work models. McKinsey reports that 71 percent of executives expect to rely more heavily on contingent workers in the coming years. This reflects a broader shift toward agility in the face of economic volatility and rapid technology change. Talent platforms are increasingly recognized as strategic infrastructure, with McKinsey even projecting that they could add up to $2.7 trillion to global GDP by 2025. Flexible work isn’t just a trend in the U.S. Many countries, particularly in Europe and the Asia-Pacific region, continue to embrace contingent work arrangements for cost efficiency and resilience.

This backdrop makes Lifted’s positioning appear timely. Yet there’s reason to question whether it’s designed to genuinely meet enterprise needs, or to better monetize procurement budgets. Quest for margin expansion, competitive positioning, or positioning Upwork’s enterprise offerings for sale might be driving this more than mission alignment.

Upwork’s Enterprise Play: A Response to Past Struggles

Upwork has wrestled with enterprise adoption before. Its prior “Enterprise” offering lived within the broader marketplace; a workable model for freelance, SMB, and tech-savvy buyers, but enterprise buyers operate differently. They seek seamless compliance, procurement integration, vendor management, and strategic partnerships. Upwork’s creation of Lifted signals a recognition that packaging enterprise services alongside the marketplace was impeding its ability to address fundamentally different buyer requirements. It’s not easy.  As challenging as it has been for the biggest player in the room, smaller marketplaces face a steeper hill to climb, because they simply don’t have the brand, scale, or infrastructure to meet broad enterprise expectations.

By creating Lifted, Upwork isn’t retreating, it’s repositioning. But the question looms: is this about re-engineering the client experience, or about carving out more share of enterprise wallets with minimal disruption to its marketplace business while positioning Lifted for sale?

The Language Shift: Contingent Workers vs. Freelancers

It’s notable that Upwork’s Lifted announcement leans hard into using “contingent workers” instead of “freelancers” or “independent workers.” Freelancers and independent workers signaled talent with autonomy, choice, entrepreneurship and human-first narratives. Contingent worker is a more generic, enterprise-preferred term that includes independent contractors, temps, EOR employees, staff augmentation and is anchored more in procurement conversations than in workforce planning.

This linguistic shift suggests Upwork is chasing procurement and operations teams more than modern HR and talent leaders. It raises the question: is this a strategic advance in modern work leadership, or a capitulation to where the money sits in enterprise organizations?

What Lifted Doesn’t Yet Solve: Adoption and Change

While Lifted aggregates all contingent workforce models under one roof, the real challenge lies in enterprise adoption and change management. Deloitte tells us that closing the “experience gap,” helping internal teams adapt to new flexible models is the hardest part of modern workforce transformation. Without embedded guidance, cultural enablement, or change frameworks, Lifted’s consolidated platform risks remaining a transactional tool rather than a transformation partner.

Conclusion: Hopeful Curiosity, with a Critical Eye

Upwork’s launch of Lifted is a notable step forward; and one that reflects real learning from past challenges in the enterprise space. It’s encouraging to see them doubling down rather than walking away, and signaling that the needs of large, complex organizations require a different structure, language, and approach than their core marketplace.

That said, it’s hard to ignore the pattern of pivots and org-shuffling, which raises fair questions about whether this is a genuine client-centric evolution or a strategic positioning to satisfy investors and prepare for a different path. The shift in language, the repositioning, and the timing all suggest both ambition and pressure.

Still, I’m interested to see what comes next. If this team can pair Lifted’s consolidated offering with the advisory, change management, and long-term thinking that enterprises truly need, it could become a meaningful force in the future of work.