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This paper is based on the cross-case analysis of case studies of eight award-winning secondary schools from across the United States that used technology as an integral part of transforming their schools. Through our analysis of interviews with over 150 educators, observations in multiple classrooms, and document analysis we uncovered eight factors that must be addressed to effectively leverage technology for school reform or school improvement. Because we found that all eight factors must be addressed simultaneously, or the effectiveness of any plan for using technology for school reform will falter or even fail, we share multiple examples of “what works” and “how it works” and discuss recommendations for leading technology-rich 21st century schools.