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

- Link: https://viralbrief.top/the-turnaround-how-weworks-ceo-used-dress-codes-and-flexibility-to-revive-the-office-giant/
- Published: 2026-10-30T08:03:15+00:00
- Author: Olamide

## 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](https://www.businessinsider.com/wework-ceo-dress-code-work-from-home-the-long-play-2026-10)

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  TL;DR (AI Generated)

Under the leadership of CEO John Santora, WeWork has successfully rebounded from
Chapter 11 bankruptcy to achieve profitability and financial stabilization.

Replacing the company's previous Silicon Valley hype, Santora introduced a disciplined,
real estate-focused management approach.

He balanced this new operational structure by implementing a professional dress 
code alongside modern flex-work policies that prioritize employee output and work-
life balance.

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