WeWork CEO John Santora says dress code and work-from-home flexibility helped change company culture

John Santora says WeWork’s turnaround requires both workplace standards and employee trust.

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.

John Santora on rebuilding WeWork's culture. (WeWork)

WeWork CEO introduces a dress code

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.

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.

"I grabbed my head of HR," he recalled. "See that? I don't want to see it anymore."

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.

"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.

Why WeWork employees can work from home on Fridays

Alongside the dress code, Santora introduced a weekly work-from-home day. He said the decision was also influenced by his own experience of struggling to balance professional responsibilities with family commitments.

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 because of work.

"I didn't have the ability to go watch my son play a 3 o'clock baseball game," Santora said. "We have to give our employees that flexibility to do all that."

Even Santora occasionally relaxes his formal dress code. While he generally prefers suits and ties, he admitted that Fridays sometimes mean wearing sneakers, depending on his schedule.

WeWork's recovery after bankruptcy

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.

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.

Santora's approach suggests that rebuilding WeWork has involved not just financial recovery but also redefining workplace expectations.