WeWork and Upwork CEOs confirm the Gen Z hiring nightmare is real—but it’s nothing new
Gen Z is experiencing significant challenges in the job market due to AI disruptions. WeWork CEO John Santora emphasizes the need for senior leaders to mentor and educate new talent. Despite concerns, Upwork CEO Hayden Brown suggests that the shift towards freelance work may provide opportunities for younger workers.
- ▪Entry-level positions are becoming scarce as companies downsize in response to AI advancements.
- ▪Santora believes that older workers can help train new talent to fill future roles as baby boomers retire.
- ▪Brown points out that the rise of freelance work offers flexibility and empowerment for workers in a changing economy.
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| Original publisher | Fortune |
| Canonical URL | https://fortune.com/2026/05/19/wework-upwork-ceo-gen-z-jobs-ai-freelance/ |
| Publication time | Tue, 19 May 2026 18:25:55 +0000 |
| Retrieval time | 2026-05-19T18:49:57.905Z |
| Last seen | 2026-05-19T18:49:57.905Z |
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| Cluster | p7y8aHyAMzvF |
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| Publisher visit | Yes — open original |
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| Retrieval / RAG | May the content be exposed for third-party retrieval-augmented generation? | Not asserted |
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Opening excerpt (first ~120 words) tap to expand
It’s no secret that Gen Z is facing the brunt of AI job disruption. Entry-level openings in fields with high AI exposure are becoming rarer as companies downsize. Recommended Video “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.
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Excerpt limited to ~120 words for fair-use compliance. The full article is at Fortune.
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