The Turnaround: How WeWork’s CEO Used Dress Codes and Flexibility to Revive the Office Giant

A New Era for WeWork

When John Santora stepped into the role of CEO at WeWork in 2024, the company was in a precarious position. Having recently emerged from a challenging Chapter 11 bankruptcy filing, the once-buzzy office-sharing startup was tasked with proving it could be a viable, profitable business. Two years later, the company has achieved a significant turnaround, reporting eight quarters of EBITDA profitability and projecting a fourth consecutive quarter of cash-flow success.

The company, which was founded in 2010 and once boasted a valuation of $47 billion before a dramatic decline, has shifted its focus under Santora’s leadership. In 2025, WeWork reported approximately $2.3 billion in revenue, signaling a stabilization that many observers once thought impossible.

From Silicon Valley Hype to Real Estate Discipline

The transition in leadership marks a stark departure from the company’s origins. Under its founder, Adam Neumann, WeWork was defined by bold, often abstract, declarations about changing the world. However, following a failed IPO and subsequent financial turmoil, stakeholders sought a leader with a more grounded approach. Santora, who spent 47 years at the real estate firm Cushman & Wakefield, brought a background defined by industry experience rather than the Silicon Valley-style magnetism of his predecessor.

“From a leadership standpoint, I’m a very structured, disciplined person,” Santora noted during a recent event at Business Insider’s The Long Play. He described himself as a “suit and tie, buttoned-up real estate person,” a persona he brought with him to the WeWork headquarters.

Balancing Decorum with Modern Flexibility

One of the first changes Santora implemented involved the company culture, specifically regarding professional appearance. During an early visit to a WeWork office, he was surprised to find employees dressed in pajamas, slippers, and shorts. He quickly took action, informing his HR department that he wanted to see a change in the office dress code.

However, Santora emphasized that his management style is not purely about rigid formality; it is about “give and take.” While he instituted a more professional dress code, he simultaneously introduced greater flexibility for staff. Recognizing the demands of modern life, he implemented a policy allowing employees to work from home one day a week.

“I didn’t have the ability to go watch my son play a 3 o’clock baseball game,” Santora said, explaining the necessity of work-life balance. “We have to give our employees that flexibility to do all that.”

Santora’s management philosophy focuses on output rather than surveillance. He noted that he does not monitor when employees arrive or depart, provided that their work is completed and clients remain satisfied. Even the CEO has adapted his own standards, occasionally opting for sneakers on Fridays depending on his schedule.

A Stabilized Future

For Santora, the decision to take the helm at WeWork was not immediate. He admitted that he had been considering retirement before his daughter encouraged him to take the position, jokingly noting that he becomes a “pain in the ass” when he has too much idle time. Today, that decision has resulted in a company that, while not reaching its previous peak valuations, has successfully pivoted to a sustainable business model. By combining the traditional discipline of a seasoned real estate executive with an understanding of modern workplace needs, Santora has helped guide WeWork back to a path of financial health.

Source: businessinsider.com