WeWork CEO John Santora has shared how he is trying to change the company’s workplace culture by bringing in greater discipline while giving employees room to manage their personal commitments. His approach includes revisiting everyday office norms and finding a balance between professional expectations and flexibility.
Alongside the dress code, Santora introduced a weekly work-from-home day. The CEO, who describes himself as a structured and disciplined leader, recalled visiting one of WeWork’s offices shortly after taking charge. What he saw did not quite match his idea of a professional workplace. Employees were wearing pyjamas, slippers and shorts, prompting him to take the matter up with his head of human resources. “See that? “We have to give our employees that flexibility to do all that. Even Santora occasionally relaxes his formal dress code. he admitted that Fridays sometimes mean wearing sneakers, depending on his schedule While he generally prefers suits and ties. Santora’s approach suggests that rebuilding WeWork has involved not just financial recovery but also redefining workplace expectations.
Santora took over as CEO in 2024, when WeWork was emerging from Chapter 11 bankruptcy proceedings. The company had suffered a dramatic fall after its valuation dropped from $47 billion in 2019 to around $8 billion. Founded in 2010, WeWork rents out office spaces to freelancers, start-ups and businesses. Its former CEO and co-founder Adam Neumann had ambitious plans to transform the workplace, but a failed IPO exposed serious problems with the company’s business model and leadership. (Also Read: Cruise ship pianist rescued after spending 9 hours treading water off California coast: ‘I thought I was gonna die’ ) The company has since made progress towards recovery. It recorded eight consecutive quarters of positive EBITDA and reported approximately $2.3 billion in revenue in 2025.
Because of work, recalling how he could not always make time to watch his son play baseball, he said employees should not have to miss important personal moments.
“I grabbed my head of HR,” he recalled. I don’t want to see it anymore.” (Also Read: Elon Musk, Bill Ackman voice support for Jensen Huang after affair admission: ‘Humans make mistakes’ ) “I don’t look at what time they leave, what time they come in,” he said, explaining that he focuses on whether employees complete their work and keep clients happy. He said the decision was also influenced by his own experience of struggling to balance professional responsibilities with family commitments. “I didn’t have the ability to go watch my son play a 3 o’clock baseball game,” Santora said.
Speaking at Business Insider’s The Long Play event on Thursday, Santora told Deputy News Chief Cadie Thompson that establishing trust and maintaining decorum were important parts of his efforts to turn the company around.
However, Santora’s approach was not about imposing strict rules without considering employees’ needs. Having spent 47 years at real estate firm Cushman & Wakefield before becoming WeWork’s CEO in 2024, he wanted to bring a more structured approach to the workplace while allowing people some flexibility.
