The W. Clement & Jessie V. Stone Foundation hosted its fourth annual convening of education grantees in the fall of 2011. Representatives from grantee organizations in Boston, Chicago, New York and the San Francisco Bay Area gathered for a day-long session to discuss common challenges they face as they attempt to grow their work and scale their impact. Case studies of two grantees—Partners in School Innovation and the Boston Plan for Excellence—served as the centerpiece for the day’s deliberations and anchored the meeting in real-life organizational growth and management issues. Discussions focused on change management, organizational development, evaluation and relationships to school districts. The report synthesizes key themes and ideas as these education leaders shared and learned from each other.