In 2011, we worked with the W. Clement and Jessie V. Stone Foundation to organize a day-long session to help education grantees probe the specific challenges and possible paths forward that education organizations face as they grow, expand their reach and work to deepen their impact. In this report we summarize key questions and recommendations from the meeting that bring to light how education organizations can better address change management, organizational sustainability, evaluation, communications and relationships with school districts. We also provide two case studies of education organizations – Partners in School Innovation and the Boston Teacher Residency — focusing on how they were able to expand their services in a sustainable way. This is one of four annual meeting summaries that share the discussions and insights of participating grantees.