In 2009, we organized a day-long session for the W. Clement and Jessie V. Stone Foundation to give their grantees the opportunity to think deeply about the challenges and considerations involved in scaling up their organizations’ work. In this report, we summarize advice from experts on how education organizations can manage issues of scale, business planning and internal infrastructure. We also provide a framework for identifying and prioritizing scaling and sustainability challenges. This is one of four annual meeting summaries that share the discussions and insights of participating grantees.