Measuring progress toward systems change, sustainable efforts that address root causes of an issue by changing policies and practices, is a difficult task for communities, evaluators, and foundations. Tracking and documenting changes in resources, power, policy, sustainable funding, structured relationships and roles, and underlying values require multi-level analyses. Systems change analysts must consider at least four “strata” at once: (1) events and trends, (2) patterns of interaction, (3) context and cultural or social models, and (4) the systems themselves. In this paper we provide a brief overview of systems change; a discussion of collaboratives as one “engine” of social change; a discussion of benchmarks and indicators of collaboratives focused on systems change; and suggestions for further research. The analysis draws upon several analytic frameworks described in the literature. We illustrate these concepts with examples from six systems change initiatives funded by The California Endowment. The need for further research is outlined.