Des Moines (Iowa) Public Schools is one of six urban districts participating in an effort to redesign the role of principal supervisors. The Wallace Foundation's Principal Supervisor Initiative provides four years of support for these districts to transform the role, which has traditionally focused on operations and compliance, into one that supports principals to be instructional leaders. Des Moines' experience illustrates how the initiative is changing leadership structures and roles, as indicated in an implementation report of the initiative (Goldring et al., 2018). It also shows how professional learning at all leadership levels is essential for improvement. In this article, Des Moines associate superintendent Matt Smith, principal supervisor Barry Jones, and project manager Ruth Wright share their experiences with "The Learning Professional."