A growing number of school districts are moving away from the idea that charter schools are the enemy. Instead, districts are breaking down barriers and openly discussing how to share resources, responsibilities, and knowledge of what works. This report explores a lesser-known form of knowledge transfer: the practice of superintendents looking beyond the usual candidate pool and hiring administrators who have seen strong successes in the charter sector. Through interviews with superintendents, the "boundary spanners" they hire, and those who work with them, we explore the impact these boundary spanners are having not only on cross-sector collaboration, but on the way a district manages its schools. If, as originally conceived, charter schools are laboratories of innovation and practice, then hiring top administrative talent from the charter sector may be one creative and efficient way to bring innovation into traditional school districts and meaningfully bridge the divide between the two sectors.