The path to principalship in Hillsborough County Public Schools in Florida is not one taken lightly. After receiving the Wallace Foundation Principal Pipeline Initiative grant, Hillsborough was one of six districts that developed a comprehensive principal pipeline based on four key components: leader standards that define the role of principal; quality selection and preservice training practices; effective hiring practices; and on-the-job evaluation and support to provide coaching and ongoing professional learning. Historically, Hillsborough's professional learning for instructional leaders was described as a one-size-fits-all, sit-and-get experience. Principals had little access to coaching and were limited in whom they could go to for support. That changed when the Florida Department of Education awarded the district an Instructional Leadership and Faculty Development grant to develop and implement a one-year professional learning pilot program for principals throughout the district for the 2015-16 school year. The model, Leaders Engaged in Accelerating Performance (LEAP UP), aligns individual principals' professional learning needs with strategies designed to address challenges unique to each district area. LEAP UP's implementation incorporated input from the chief of schools, the executive director of leadership and development, area superintendents, and principal coaches. This article discusses the intended outcomes of LEAP UP; planning and development; external evaluation of LEAP UP; how evaluators collected data on LEAP UP; principals' assessment of LEAP UP; and LEAP UP's impact on students. LEAP UP had a positive impact on student learning in 2016. In Area 4, 92% of teachers responding to the Teaching, Empowering, Leading and Learning survey said that the professional development enhanced teachers' abilities to improve student learning, up from 62% in 2015. Additionally, 90% said that professional development enhanced teachers' ability to implement instructional strategies that meet the diverse student learning needs, up from 58%. Hillsborough County's LEAP UP implementation shows that investing in the professional learning of its school leaders leads to a more effective and enhanced school learning experience for all.