How WeWork’s latest CEO changed the company—and how it changed him

John Santora took over as CEO of WeWork in June 2024, immediately noticing the company's relaxed dress code. Staff members were dressed in everything from jeans to slippers and shorts, deviating from Santora's more traditional attire. As a long-time executive at Cushman & Wakefield, Santora believed the dress code needed adjustment. He admitted, "I'm a suit-and-tie, buttoned-up real estate person, but I'm good now."

Santora took the helm of WeWork at a pivotal time, as the company had just emerged from Chapter 11 bankruptcy. The once high-flying co-working business, which had reached a $47 billion valuation in 2019, had collapsed under the weight of costly leases, losses, and a failed IPO. A bankruptcy restructuring eliminated over $4 billion in debt and reduced future rent obligations by about $12 billion.

Since joining WeWork, Santora has worked to transform the company into a more disciplined and financially sustainable business while preserving its unique model. He has given regional presidents responsibility for profitability and tweaked the company's design to move away from its informal, loud aesthetics. However, the most significant challenge has been restoring trust with employees, clients, and landlords.

To rebuild trust, Santora held meetings with workers to explain his plans and assure them of the company's financial stability. He has leveraged his extensive network from his time at Cushman & Wakefield to maintain strong relationships with clients and landlords. In 2025, WeWork returned to profitability, reporting $2.3 billion in revenue. Santora believes the company is well-positioned to thrive amid current economic uncertainty, noting that its flexibility in space and employee numbers is a key strength.

For Santora, rebuilding WeWork has been about finding the right balance between structure and flexibility. He has learned the importance of being adaptable, a lesson he had initially overlooked.