This article reports findings from a study that explores how Teach For America (TFA) alumni interpret the causes of and interventions for educational inequality, the leadership pathways for remedying inequality, and the career opportunities available to them as TFA affiliates. Analyzing data from 117 alumni interviews, we find that the majority of participants attribute the roots of educational inequality to perceived managerial shortcomings of the public school system. We also demonstrate how TFA alumni embrace largely managerial, technocratic responses to inequality. Finally, we reveal how the majority of alumni who work in education do so in privatized settings that emphasize management, entrepreneurship, and accountability. These findings contribute to the literature on school reform, the politics of educational policy and leadership, and the discourse and policy environment in which the organization is embedded.