The purpose of this research was to understand ways exemplary award winning secondary school leaders have transformed their schools for twenty-first-century education and student achievement. This article presents three diverse case studies and identifies ways that each school's leader and leadership team reconfigured its culture and expectations, in particular by using twenty-first-century technologies as one leverage point. Qualitative data, collected through interviews, observations and document analysis, revealed multiple factors these cases shared but also articulated unique ways each of these leaders approached his/her school's individual culture, circumstances and issues. This study offers insight into the challenges current school leaders face, and the skills required to leverage technology to improve student engagement and achievement.