The Barr Foundation's Engage New England (ENE) initiative was an effort to catalyze high school innovation by developing exemplary schools that support the success of students who are off track to graduate. Grounded in the tenets of positive youth development, the ENE initiative provided grants and technical assistance to support new or redesigned schools in creating rigorous and purposeful educational programs for students who have not experienced success in traditional high schools. Through ENE, the foundation sought to demonstrate how student-centered schools can meet the varied needs of students, especially historically underserved students, and ensure their postsecondary success. This brief presents lessons learned about school transformation from the foundation's experience supporting three cohorts of grantees. The insights gained from the ENE initiative can inform reform efforts in all high schools.