WeWork CEO John Santora on stitching the company back together

Santora’s strategy for stabilizing the firm focuses on a blend of rigid decorum and pragmatic flexibility. During a recent event hosted by Business Insider, he recounted his initial shock upon visiting a WeWork office and finding staff dressed in loungewear. His directive to HR was immediate: the casual culture had to end. He now demands professional attire for key meetings, framing the shift as a necessary step toward building a sense of purpose and structure within the organization.

This discipline is balanced by a shift in how he measures productivity. Santora, who spent 47 years in the real estate industry, rejects the traditional obsession with office hours. Instead, he grants employees one day of remote work each week, citing his own desire to have balanced his career with his children's extracurricular activities. For Santora, the goal is simple: keep clients satisfied and ensure the work is done, regardless of the clock. The results suggest the approach is working. Following a period where the company's valuation plummeted from $47 billion to $8 billion, WeWork has posted eight quarters of EBITDA profitability and reported approximately $2.3 billion in revenue for 2025. Even the CEO has adapted, allowing himself the rare concession of wearing sneakers on Fridays.