Condé Nast, the publishing powerhouse behind titles such as Vogue, Vanity Fair, and The New Yorker, is seeking a new chief executive officer amid concerns about the company’s future and the dominant influence of its longtime editorial leader, Anna Wintour. Insiders describe Wintour, who holds the title of global chief content officer, as a central figure whose approval is essential for navigating the company’s complex leadership dynamics.

Wintour, who has served as editor-in-chief of Vogue for 38 years, has expanded her influence beyond the U.S. edition to exert considerable control over Condé Nast’s international business and editorial strategy. Her promotion to global chief content officer in 2020 granted her broad authority, including the ability to hire top editorial personnel across the company’s portfolio.

Sources inside Condé Nast characterize Wintour’s leadership style as exacting and politically astute, with one former executive describing her as “Machiavellian” and noting that compliance with her vision is a near prerequisite for senior management. The former executives say Wintour represents the apex of a corporate pyramid, where Vogue’s operations have increasingly overshadowed the rest of the company’s brands. “Condé Nast has become Vogue. At this point,” one source commented.

The company has undergone significant restructuring in recent years, particularly under former CEO Roger Lynch, who left last year for Mattel. Lynch’s tenure was marked by a consolidation of Condé Nast’s brand portfolio—folding Teen Vogue and Vogue Business into Vogue, merging Pitchfork into GQ, and closing or scaling back other publications such as Self, Glamour, and Allure. These moves narrowed the company’s offerings and led to the winding down of many international publishing operations.

Former executives expressed skepticism about the company’s prospects and the attractiveness of the CEO position, describing the business as “a disaster” and warning that the company has been “run into the ground.” One expressed uncertainty about who would be willing to take the helm under the current conditions.

The leadership challenge is further complicated by Wintour’s close relationship with Steven Newhouse, chairman of Condé Nast’s parent company, Advance Publications, which sources say has helped secure her influence within the organization. Wintour has also faced criticism in the past for her decisions, including her support for fashion designer John Galliano, whose controversial past stirred backlash and led to his departure from a Met Gala exhibit earlier this year.

Condé Nast did not respond to requests for comment. As the company searches for a new CEO, industry insiders note that the ability to navigate Wintour’s significant sway will be critical in shaping the publisher’s next chapter.