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The success and failure of education reform policies often depend on the strategies of reformers. This article suggests a framework to understand the positionality of reformers, as they vary in their strategy (i.e., technical vs. relational) and focus for change (i.e., process- vs. outcomes-focused). Using the case of individuals who initiated new data systems in Chicago, Philadelphia, and New York City, the study discusses four groups of reformers: Engineers privilege efficient technical fixes that may be resisted by people on the ground. Capacity-builders focus on empowering schools but may lead to variable successes. Framers research and disseminate ideas to reframe policy and political discourses. Table-setters leverage their social networks and financial resources but may challenge democratic decision-making. As schools continue to be sites of political debates and challenges, the concept of positionality can clarify how reformers promote particular changes and can suggest possibilities for positions to constructively complement each other.