When WeWork CEO John Santora assumed leadership in June 2024, he noticed a few wardrobe choices that clashed with his old-school aesthetic.
“It was the middle of June, and [WeWork staffers were wearing] everything from jeans to pajamas and slippers and shorts and so forth,” he told Business Insider.
Santora, who spent 47 years at Chicago-based commercial real estate giant Cushman & Wakefield, decided the dress code needed some changes. “There are a lot more sport jackets around the office,” he said.
And Santora has learned to loosen up a bit. “On Fridays, I’ll actually sometimes wear sneakers,” he said. “I’m a suit-and-tie, buttoned-up real estate person, but I’m good now.”
Santora took the helm of WeWork just as it emerged from Chapter 11 bankruptcy, following years of financial turmoil and controversy under cofounder Adam Neumann.
The once-high-flying co-working company had become a cautionary tale of unchecked growth, reaching a $47 billion valuation in 2019 before collapsing under the weight of costly leases, mounting losses, and a failed initial public offering. WeWork’s bankruptcy restructuring, which was completed shortly before Santora arrived, eliminated more than $4 billion in debt and reduced its future rent obligations by about $12 billion.
Santora has since sought to transform the company into a more disciplined, financially sustainable business while preserving its fundamental model, which he still sees as a valuable alternative to traditional corporate real estate.
One change was to give regional presidents responsibility for profitability, as opposed to just sales and operations. He has also tweaked the company’s design, nudging it away from the informal, loud aesthetics of its early days toward a quieter, more corporate style.
But the biggest challenge has been restoring trust from employees, clients, and landlords. Santora has held meetings with workers to explain his plans and assure them that the company has sufficient capital to meet payroll and rent obligations. For clients and landlords, he has drawn on many of the relationships he built over decades at Cushman & Wakefield.
WeWork returned to profitability in 2025, reporting $2.3 billion in revenue, and Santora thinks it is poised to thrive amid current economic uncertainty.
“Not knowing how much space you need or how many employees you’re going to have—that is kind of in our sweet spot,” Santora said. At present, about 300 artificial intelligence companies occupy WeWork spaces worldwide, ranging from tiny startups to large brand-name businesses, he noted.
For Santora, rebuilding the company has meant balancing structure and discipline with the versatility that made the company appealing in the first place. That balancing act has taught him something he hadn’t fully appreciated: the importance of being flexible.
“I mean, I saw it, but now I live it. And I see how important it is,” he said.