The Learning Forward Academy is Learning Forward's flagship deep learning experience, committed to increasing educator and leader capacity and improving results for students in the ever-changing landscape of education. For over 30 years, the academy has supported the problem-based learning of teachers, teacher leaders, instructional coaches, principals, regional leaders, superintendents, and others whose jobs involve supporting the learning of other adults and students. The academy brings together educator leaders with expert coaches to create successful and sustainable change in their educational systems. Over the professional learning program's 2 and a half years, participants learn about and implement several system improvement tools, such as root cause analysis and theory of change, and work together on their individual problems of practice. At the core of the academy is an understanding that educational improvement is iterative and requires continuous assessment, adaptation, and refinement, as well as ongoing learning among all educators in a system. This article examines how a principal was able to use the lessons she learned at the academy to improve reading grade levels and combat chronic absenteeism at her school in New Jersey.