WeWork and Upwork CEOs confirm Gen Z hiring struggles are real—but not unprecedented

(SeaPRwire) –   Gen Z is clearly bearing the brunt of job disruption driven by AI. Entry-level positions in industries most exposed to artificial intelligence are increasingly scarce as companies continue to downsize.

“There’s no question that entry-level hiring is under significant pressure,” WeWork CEO John Santora stated during an interview at the Workplace Innovation Summit on Tuesday. He emphasized that senior leaders have a responsibility to help address this challenge.

“It’s up to all of us to bring in this talent and educate them, teaching them how to become the future growth engine for our organizations,” Santora told Phil Wahba, senior writer. “AI can’t provide the empathy, leadership, mentoring, and other essential skills required to successfully lead a company.”

Santora’s career path may seem nearly impossible for today’s Gen Z workers. He spent 47 years at Cushman & Wakefield, advancing from building engineer to chief operating officer. Just as he was preparing to retire, WeWork recruited him in 2024, launching his second career and helping steer the once-bankrupt company toward profitability. He observes that older workers are now taking advantage of increased longevity to reinvent themselves around age 60 or 65—just as he did—while also training emerging talent.

Despite the uncertainty facing Gen Z in the labor market and mixed signals about how AI will reshape work, Upwork President and CEO Hayden Brown maintains an optimistic outlook.

“The hype around AI is real,” Brown acknowledged. “But the fear-mongering creates significant challenges, not only generating uncertainty but making employees wonder about their own role.” She notes, however, that data tells a different story: companies are engaging in what she calls “AI-washing”—using AI as an excuse to reduce headcount amid economic volatility. A recent National Bureau of Economic Research study found that nearly 90% of C-suite executives report that AI has had zero impact on employment since ChatGPT’s launch in November 2022.

Santora concurred, offering a broader historical perspective on workforce disruptions.

“We’ve always gone through these cycles with new technological or industry changes,” he explained. With AI adoption, companies will become more productive and ultimately grow, leading to increased hiring over time.

“Baby boomers are retiring, so there’s opportunity to fill those roles going forward,” Santora added. “I’d look at it with optimism if I were 25 years old.”

The rise of freelancing

The traditional 9-to-5 workplace standard is becoming obsolete. Brown, who leads one of the largest freelance platforms, observes that each generation shows growing interest in freelance and contingent work arrangements.

“This provides people with freedom, flexibility, and empowerment to shape their careers according to their own terms,” she said.

Santora believes greater employee flexibility fosters stronger accountability. At WeWork, employees are required to be onsite three to four days per week, though he acknowledges that “life inevitably interferes.” Workers need flexibility for doctor’s appointments and childcare or elder care responsibilities—if employers don’t offer it, they’ll simply find jobs that do, he explained.

The era where workers juggle three or four jobs simultaneously to make ends meet has arrived, Brown noted, and this multi-job approach might actually help drive AI adoption. Freelancers are uniquely positioned to navigate AI-related uncertainty because they’re “intrinsically motivated to quickly sell skills and upgrade their capabilities faster than full-time employees,” she explained.

Upwork is seeing businesses increasingly turn to freelance workers because they typically require less training on AI tools, and AI-related skills command a 40% premium in today’s market, Brown said.