Though women are increasingly breaking the glass ceiling into the position of school superintendent, the profession continues to be predominately occupied by men. More historical biographs of successful female superintendents may encourage women to pursue the role. To that end, this study examined the impact of a progressive-era trailblazer for women in educational leadership, Susan Miller Dorsey, superintendent of Los Angeles City Schools from 1920 to 1929. Two critical questions were addressed: What factors influenced Dorsey? Can her experiences in administration reveal any critical influences for present-day female teachers who pursue administrative positions?