WeWork and Upwork CEOs confirm the Gen Z hiring nightmare is real—but it’s nothing new

“There’s no question that the entry-level hire is under pressure,” WeWork CEO John Santora said in an interview at Fortune’s Workplace Innovation Summit on Tuesday. It’s up to senior leaders to help solve the problem.

“It’s incumbent upon all of us to bring that talent in and to educate the talent and teach them to be the future growth of all our organizations,” he told Fortune senior writer Phil Wahba. “AI is not going to provide empathy and leadership and mentoring and all those skills that you need to lead a company for a company to be successful.” 

Santora has a career that seems unimaginable for Gen Z workers. He worked at the real estate firm Cushman & Wakefield for 47 years, rising from building engineer to chief operating officer. He was ready to retire when WeWork came calling in 2024, launching him into a second career as he steered the once-bankrupt company to profitability. He sees older workers taking advantage of increased longevity to reinvent themselves at 60 or 65, as he did, and to train new talent. 

Even as Gen Z faces a labor market mired in uncertainty, receiving mixed signals about how AI will reshape the future of work, Upwork President and CEO Hayden Brown is not doom-and-gloom. 

“The hype is real,” Brown said. “The fear-mongering is a real challenge because it does create a lot of this, not just uncertainty, but I think employees are really wondering what their place is.” But, she says, the data tells another story, and companies are “AI-washing” their need to shrink their workforce in a “volatile economy.” A recent National Bureau of Economic Research study found that almost 90% of C-suite executives say that AI has had no impact on employment since the release of ChatGPT in November 2022.  

Santora agreed and took a broader look at the history of workforce disruption. 

“We go through these cycles and have, and every time there’s a new technology change or an industry change.” With AI, companies will become more productive and grow, which will eventually lead to more hiring, he explained. 

“The baby boomers are retiring, so there’s an opportunity to fill those spots going forward,” Santora later added. “I would look at it with bright eyes if I was 25.” 

The freelancer era

Gone are the days of a traditional 9-to-5 being the workplace standard. Brown, who runs one of the largest freelance marketplaces, said that with each generation, she sees more people turning to freelance and contingent work. 

“This is what gives people the freedom, the flexibility, and empowerment to run their career on their own terms,” she said. 

Santora says that giving employees more flexibility leads to greater accountability. At WeWork, employees are required to come in three or four days a week, but he recognizes “life gets in the way.” Workers need the flexibility for doctor’s appointments and child or parental care because if you don’t give it, they’ll find a job that does, he explained. 

The era of workers splitting themselves between three or four different jobs to earn a living is here, Brown said, and it may be the answer to getting workers to adopt AI. Freelancers are well-positioned to weather AI uncertainty because they are “intrinsically motivated to sell skill and upskill much faster than in-house employees,” she explained. 

Upwork is seeing businesses turn more to freelance workers because they typically don’t have to train them on AI tools, and AI skills are going at a 40% premium in the market, she said.