This paper offers lessons learned about what it takes to successfully leverage technology for school improvement based on a cross-case analysis of eight award-winning secondary schools/districts around the United States. The researchers analyzed data from 150 interviews, 30 focus groups, and more than 300 hours of observation in 150 classrooms, plus extensive document analysis, to reveal numerous lessons learned across the eight sites. Findings from this study indicated that eight factors must be addressed (nearly) simultaneously when technology is used as a lever for school reform: vision, distributed leadership, technology planning and support, school culture, professional development, curriculum and instructional practices, funding, and partnerships. Implications for current and future practice include important lessons for university and district-based technology specialists, educational researchers, and school and district leaders about taking a systems approach when considering technology among these factors needed for comprehensive school reform efforts to be sustained.