WeWork CEO John Santora on Rebuilding Culture With a Dress Code and Remote Work Flexibility

When John Santora took over as chief executive of WeWork in 2024, the company was only just emerging from a Chapter 11 bankruptcy filing that closed a chapter on one of the most spectacular reversals in recent startup history. The office-sharing firm, once valued at roughly $47 billion, had lost most of that value after a failed initial public offering, a collapse in investor confidence, and a leadership style that many stakeholders came to view as unsustainable. Santora’s task was not simply to cut costs or renegotiate leases. It was to rebuild the internal culture of an organization whose identity had been shaped by its founder’s ambitions. At Business Insider’s The Long Play event, he explained how he approached that problem, and his answer centered on something less glamorous than vision statements: trust, decorum, and a deliberate balance between structure and flexibility.

The Background: From Unicorn to Restructuring

WeWork was founded in 2010 as a company that leased large blocks of commercial real estate, renovated them, and subdivided the space into flexible memberships for freelancers, startups, and established firms. This model, often described as flexible workspace or coworking, was not new, but WeWork distinguished itself through aggressive expansion, branding, and a narrative that framed the business as a technology platform rather than a property operator. Under founder Adam Neumann, the company made sweeping claims about its mission, including the goal to “elevate the world’s consciousness,” and it attracted large investments on the strength of that story.

The business model carried a structural vulnerability. WeWork signed long-term leases with landlords while selling shorter-term memberships to its customers. This mismatch between liabilities and revenue meant that any slowdown in demand or tightening of capital markets could quickly produce severe financial strain. When WeWork attempted to go public in 2019, scrutiny of its financial disclosures, governance arrangements, and related-party transactions led to a sharp reassessment of its value. The planned offering was withdrawn, Neumann stepped down, and the valuation fell sharply in the months that followed. The company later filed for Chapter 11 protection, a process that allowed it to restructure its obligations and emerge with a smaller footprint and new ownership.

Understanding this history matters because the cultural problems Santora inherited were not separate from the financial ones. Observers of the period frequently pointed to a corporate environment in which informality, rapid growth, and charismatic leadership overshadowed operational discipline. Restoring confidence therefore required changes in how the organization behaved as well as how it was financed.

A Different Kind of Leader

Santora arrived with a background that contrasted sharply with the founder’s public persona. He had spent nearly five decades at Cushman & Wakefield, a major commercial real estate services firm, where he served as chief operating officer before joining WeWork. His experience was rooted in lease management, property operations, and the mechanics of institutional real estate rather than in technology startup culture. Describing his own style, he characterized himself as “a very structured, disciplined person,” adding with some self-deprecation that he was “a suit and tie, buttoned-up real estate person.”

This contrast is analytically useful. Founder-led companies often rely on the personal energy and vision of a single individual to motivate employees and investors. When that individual’s judgment comes under question, the organization may lack the procedural safeguards needed to correct course. A leader drawn from operational or financial backgrounds typically emphasizes process, accountability, and measurable performance. Whether that orientation is ideal for a company that still wants to position itself as innovative is an open question, but in the specific context of a turnaround, predictability and discipline can be more valuable than charisma.

Santora also indicated that the decision to join was not automatic. He described being at a point where retirement was a serious option, and he credited a family conversation with pushing him toward accepting the role. Such personal considerations are rarely discussed in corporate case studies, yet they illustrate the risks that turnaround executives take when they commit to organizations with uncertain futures.

Dress Code and Decorum as Cultural Signals

The most striking detail from Santora’s remarks concerned attire. During an early visit to one of WeWork’s offices, he reported seeing employees in jeans, pajamas, slippers, and shorts. His response was to bring the matter to the head of human resources and to require a change. He described the reaction in blunt terms: he did not want to see that anymore.

On its surface, a dress code may appear trivial relative to debt restructuring or revenue growth. However, workplace norms serve as visible indicators of expectations. Standards of appearance, punctuality, and conduct communicate what leadership values and how seriously it treats the enterprise. In a company trying to convince clients, landlords, lenders, and investors that its problems were behind it, the signal sent by employees’ presentation at client-facing sites carries practical weight. Organizational sociologists have long noted that small rituals and visible rules shape group identity, and a turnaround leader may use such rules deliberately to mark a break with the past.

There is, however, a counterargument. Critics of heavy dress regulation argue that it can alienate talent, particularly in technology and creative sectors where informality is associated with productivity and openness. Mandating formal wear may also signal distrust. Santora addressed part of this tension by noting that the policy was not rigid. He said he did not monitor arrival and departure times and was focused on whether employees were completing their work and keeping clients satisfied. This suggests an outcome-based philosophy: standards of appearance and presentation are maintained, while day-to-day oversight is limited to results.

Balancing Standards and Autonomy

The combination of formal expectations and output-based evaluation reflects a broader management approach that has gained attention in both corporate and remote-work research. Studies of hybrid and flexible arrangements have repeatedly found that employee trust and perceived fairness influence engagement as much as the specific rules themselves. A rule that is clearly justified and consistently applied is generally accepted more readily than one that appears arbitrary. The effectiveness of Santora’s approach will therefore depend less on the dress code itself than on whether employees perceive it as connected to client service and professional credibility.

Flexibility, Remote Work, and the Return-to-Office Debate

Santora also described a policy allowing employees one day per week to work from home. He tied this decision to his own family obligations, recalling that he had once been unable to attend his son’s afternoon baseball game and insisting that employees should have comparable flexibility. This personal anecdote connects to a much larger debate about return-to-office mandates that gained intensity after the pandemic.

The contradiction is notable. WeWork’s business is built on the premise that people need physical workspace, yet the company’s own internal policy includes remote work. For many observers, this is not a contradiction at all. Flexible office providers succeed when they offer members a range of options, including dedicated desks, private suites, and occasional use of shared space. An employer that recognizes the value of flexibility internally may be better positioned to understand the needs of its customers. Nonetheless, critics could argue that a company selling office space has an incentive to promote in-person work, and that a hybrid policy may reflect a compromise rather than a principled stance.

The broader evidence on hybrid work remains mixed and contested. Some research has associated remote or hybrid arrangements with higher retention and reduced commuting burdens, while other analyses have raised concerns about mentorship, collaboration, and the visibility of junior employees. Companies differ widely in their approaches, and outcomes depend heavily on job type, management practice, and team structure. A single weekly remote day is one of the more moderate models, and its effects would need to be evaluated against measures such as productivity, attrition, and employee satisfaction rather than assumed to be beneficial in every case.

The Financial Turnaround in Context

Santora’s cultural agenda has to be assessed alongside the company’s financial performance. According to figures cited in the source reporting, WeWork has posted eight consecutive quarters of positive EBITDA and expects a fourth straight quarter of positive cash flow. It reported approximately $2.3 billion in revenue in 2025. These results indicate that the company has moved from crisis management toward sustainable operations, although they do not by themselves reveal whether the underlying business model is now robust under adverse conditions.

EBITDA, which measures earnings before interest, taxes, depreciation, and amortization, is a common metric for comparing operating performance, but it can present an incomplete picture for businesses with heavy lease obligations. A company that has restructured its lease commitments may show improved EBITDA while still carrying significant fixed costs. Investors therefore often examine cash flow, debt levels, and lease liabilities alongside headline profitability. Readers evaluating the turnaround should treat these indicators as evidence of stabilization rather than as proof of long-term viability.

The valuation history is equally instructive. The decline from about $47 billion to roughly $8 billion during the 2019 crisis illustrates how quickly perceptions of a company can change when governance and financial transparency are called into question. Rebuilding credibility is therefore not only a matter of operational improvement but also of consistent, verifiable behavior over time.

Expert Perspectives and Remaining Questions

Commentators generally agree that WeWork’s recovery depended on addressing excessive expansion, weak unit economics, and governance failures. There is less consensus on whether a company centered on flexible office space can achieve the scale and margins its early investors anticipated. Some analysts view the flexible workspace sector as a durable part of the commercial real estate market, particularly for small firms and mobile workers. Others argue that the category is structurally thin-margined and vulnerable to shifts in corporate real estate strategy, especially if large employers reduce their footprints.

Santora’s leadership style raises a separate question. A disciplined, process-oriented executive may be well suited to stabilization, but growth often requires experimentation and risk tolerance. Whether the company can combine operational discipline with the capacity to innovate in products, pricing, and services will shape its trajectory. Cultural measures such as dress codes and flexible scheduling may improve internal cohesion, but they do not in themselves answer strategic questions about market positioning or competitive advantage.

Practical Lessons for Leaders in Turnaround Situations

Several practical lessons emerge from Santora’s account. First, visible standards can be useful when an organization needs to reset expectations, provided they are explained in terms of client service and professional purpose. Second, flexibility works best when it is linked to measurable outcomes rather than to surveillance of working hours. Third, personal credibility matters: leaders who restore trust often do so by showing consistency between what they require of others and how they conduct themselves. Santora’s acknowledgment that he wears sneakers on some Fridays suggests an attempt to maintain structure without appearing rigid, although it also shows that the boundaries of the policy are negotiated rather than absolute.

Executives facing similar situations should monitor several indicators: employee retention in critical roles, client satisfaction and renewal rates, the relationship between operating results and cash generation, and the perceived fairness of internal policies. Culture change is slow to measure, but its effects appear in hiring, performance, and reputation over time.

Frequently Asked Questions

What did WeWork’s CEO change about company culture?

John Santora introduced a dress code for employees and allowed one day per week of remote work. He also emphasized trust, decorum, and accountability based on work output and client satisfaction rather than on monitoring working hours.

Why did WeWork file for bankruptcy?

WeWork filed for Chapter 11 bankruptcy after a failed initial public offering, a sharp decline in valuation, and mounting financial pressure caused by long-term lease obligations and rapid expansion. The restructuring allowed the company to reorganize its debts and continue operating.

Is WeWork profitable now?

According to the reporting cited, WeWork has posted eight quarters of positive EBITDA and expects a fourth straight quarter of positive cash flow. Profitability measures should be interpreted carefully, since EBITDA does not capture all costs, including lease obligations.

Does WeWork allow remote work?

Santora described a policy giving employees one day per week to work from home, which he presented as a way to provide flexibility for personal responsibilities.

What Comes Next for WeWork and Flexible Work

The most important insight from Santora’s account is that WeWork’s recovery depends on two forms of credibility that reinforce each other. The first is financial: demonstrating that the business can generate cash without relying on unsustainable growth. The second is cultural: convincing employees, clients, and the market that the organization has replaced improvisation with disciplined execution. A dress code and a flexible workday are modest tools, but they signal an effort to build predictable norms in place of the founder-centered culture that preceded the collapse. Whether that effort is sufficient will become clearer as the company faces its next test, whether a downturn in office demand, a shift in corporate real estate strategy, or intensifying competition from traditional landlords offering their own flexible products. The unresolved question is whether a company built on the promise of reinventing work can succeed by becoming, in some respects, more conventional. If it can, the case may offer a template for how flexible-work firms mature; if it cannot, the episode may show that stability and disruption are harder to reconcile than either side of the debate has admitted.