Over the past decade, communities nationwide have used federal Promise Neighborhoods grants to develop cradle-to-career solutions, or “pipelines,” to produce better results for children and youth. Although their communities, populations, and circumstances are unique, Promise Neighborhoods grantees share a common approach (being driven by data and evidence and fostering deep collaboration) and a common aspiration (to achieve population-level changes in a set of results from early childhood to young adulthood). Promise Neighborhoods also share leadership challenges and opportunities that arise from carrying out an enterprise with such large scope and scale. This brief explores how a leadership development program supports Promise Neighborhoods grantees in their efforts to achieve population-level results. This brief highlights frameworks, tools, and reflections on challenges and opportunities in using leadership development to advance results in a complex initiative, as well as a unique partnership and approach to federal training and technical assistance.