WeWork CEO’s Culture Reset: Dress Code, Flexibility and a Push for Discipline

John Santora became WeWork’s CEO in 2024, shortly after the company emerged from Chapter 11 bankruptcy. At Business Insider’s The Long Play event, he said rebuilding WeWork involved creating a stronger sense of trust and decorum among employees. His approach leaned on structure and discipline, shaped by his long real estate background at Cushman & Wakefield.

Santora said he instituted a dress code after seeing employees wearing jeans, pajamas, slippers, and shorts during an early office visit. He described himself as a “suit and tie, buttoned-up real estate person,” and wanted that mindset reflected in key workplace moments. The takeaway for leaders: visible standards can reset expectations quickly, but they work best when tied to a broader culture goal.

The culture reset was not only about stricter rules. Santora also gave employees one day a week to work from home, saying workers need flexibility for life responsibilities such as attending a child’s afternoon baseball game. He said he does not focus on when employees arrive or leave as long as they get their work done and keep clients happy.

WeWork has stabilized from its 2019 crisis, when its valuation fell from $47 billion to roughly $8 billion before a bailout. The company posted eight quarters of EBITDA profitability and expects a fourth straight quarter of cash-flow profitability, according to the Business Insider report. In 2025, WeWork reported about $2.3 billion in revenue, showing that the company’s recovery is being measured not just in culture, but in financial performance.

WeWork was founded in 2010 and built its business by renting office space, improving it, and leasing it to freelancers, startups, and other companies. Under founder Adam Neumann, the company became known for ambitious language about changing the world, but its failed IPO exposed deeper problems. Santora’s style appears intentionally different: less Silicon Valley spectacle, more real estate discipline, with even his occasional Friday sneakers framed as an exception to the rule.