WeWork's New CEO Traded Pajamas for Sport Jackets — and Mondays at Home

WeWork returned to profitability in 2025 on roughly $2.3 billion in revenue, according to CEO John Santora — and he credits part of the turnaround to a trade: fewer pajamas at the office, more flexibility everywhere else.

Santora became CEO in June 2024. On an early office visit, he told a Business Insider event, he noticed employees dressed in everything from jeans to pajamas, slippers, and shorts. After 47 years at Cushman & Wakefield, he describes himself as a suit-and-tie, buttoned-up real estate person. He took the observation to the head of HR and said he did not want to see it anymore. WeWork now has a dress code.

He did not impose a uniform. Santora frames the change as give and take, and says there are simply a lot more sport jackets around the office than before.

What did employees get in return?

The other half of the policy carries the weight. Santora lets employees work from home one day a week and says he does not check what time they arrive or leave. In his words, the only conditions are that they get their work done and keep their clients happy.

He ties that flexibility to personal regret, recalling times he could not go watch his son play a baseball game at 3 o'clock. He hoped employees would have room for those moments. He also joked that on Fridays he sometimes wears sneakers, depending on his schedule.

The caveat is obvious: a dress code plus one remote day is a modest bargain by current corporate standards, and Santora's account of it comes from his own platform appearances, not from employee feedback. No survey or retention data accompanied the anecdote.

Why did trust need rebuilding at all?

WeWork's recent history explains the stakes. The company hit a valuation of $47 billion in 2019, then collapsed under costly leases, mounting losses, and a failed IPO. The bankruptcy restructuring, completed shortly before Santora arrived, eliminated more than $4 billion in debt and cut future rent obligations by about $12 billion — roughly three times the debt reduction in ongoing lease savings.

According to Fast Company, Santora's biggest challenge was restoring trust among employees, clients, and landlords. He held meetings with workers to explain his plans and to assure them the company had enough capital to meet payroll and rent. He also leaned on relationships built over decades at Cushman & Wakefield to reassure clients and landlords — an asset no restructuring document can replicate, and one that lived or died on his personal credibility.

How is the business actually run now?

Santora changed the operating structure too. Regional presidents now carry responsibility for profitability, not only sales and operations. He has also nudged WeWork's design language away from the loud, informal style of its early years toward something quieter and more corporate — a visual signal that the company is courting a different customer than the beer-tap startup crowd of 2019.

The results, so far, are the numbers: profitability in 2025 and about $2.3 billion in revenue. What remains unsaid is how durable that profit is against a lease portfolio the company spent $12 billion to shrink, or whether a sport-jacket culture can hold talent in a market where rivals offer fully remote roles.

The takeaway in plain words: Santora bought credibility with a dress code, but the restructuring — $4 billion of debt gone and $12 billion in rents shed — is what paid for it.