Organizational crises, such as the COVID-19 pandemic, influence the appointment of leaders from underrepresented groups, including women and people of color. This study examines the relationship between the pandemic, school organizational characteristics, and the appointment of women and people of color to school leadership (e.g., Head of School, HoS) roles. Using administrative data from the Data Association for Schools and Leadership (DASL) provided by the National Association of Independent Schools (NAIS), we employed two analytic approaches: single-group interrupted time series analysis and a two-way fixed effects model. Findings indicate a significant post-pandemic increase in the representation of women, people of color, and women of color in head-of-school positions. Additionally, minority heads were more likely to serve in schools that were smaller in size, showed a lower yield rate, and had more indicators of financial duress, such as higher proportions of students applying for financial aid. Changes in the likelihood of a woman or person of color HoS were also linked to teacher attrition and increased diversity on school boards. These findings offer theoretical and empirical contributions to understanding and advancing diversity in educational leadership.