As schools and classrooms explore technology-based, student-centered, personalized approaches to teaching and learning, their efforts to innovate can be hamstrung by archaic district operating systems that do not allow them to take advantage of new technologies, to work with smaller startup companies, or to quickly make and implement decisions. When he was at the helm of the New York City Department of Education (NYCDOE), Chancellor Joel Klein attempted to remedy this problem by creating the iZone, an office explicitly charged with fostering innovation from within the school district. From 2012 to 2014, the author designed and served as executive director of Innovate NYC Schools, the iZone project that focused on new structures for district procurement and decision making. As the first urban school system to make design thinking a routine part of its practice with educators, alternatives were created to established procurement processes and build collaborations between the school district and early-stage education technology companies. Regular support was also provided to entrepreneurs, investors, and innovators who sought to do business with NYCDOE. Using the philosophy and examples from NYCDOE, this paper lays out steps school systems can take to foster innovative practices throughout the organization and develop new instructional tools and practices through nimble procurement procedures.