Place-based initiatives attempt to reduce persistent health inequities through multisectoral, cross-system collaborations incorporating multiple interventions targeted at varying levels from individuals to systems. Evaluations of these initiatives may be thought of as part of the community change process itself with a focus on real-time learning and accountability. We described the design, implementation, challenges, and initial results of an evaluation of the West Philly Promise Neighborhood, which is a comprehensive, child-focused place-based initiative in Philadelphia, Pennsylvania. Priorities for the evaluation were to build processes for and a culture of ongoing data collection, monitoring, and communication, with a focus on transparency, accountability, and data democratization; establish systems to collect data at multiple levels, with a focus on multiple uses of the data and future sustainability; and adhere to grant requirements on data collection and reporting. Data collection activities included the compilation of neighborhood-level indicators; the implementation of a program-tracking system; administrative data linkage; and neighborhood, school, and organizational surveys. Baseline results pointed to existing strengths in the neighborhood, such as the overwhelming majority of caregivers reporting that they read to their young children (86.9%), while other indicators showed areas of need for additional supports and were programmatic focuses for the initiative (e.g., about one-quarter of young children were not engaged in an early childhood education setting). Results were communicated in multiple formats. Challenges included aligning timelines, the measurement of relationship-building and other process-focused outcomes, data and technology limitations, and administrative and legal barriers. Evaluation approaches and funding models that acknowledge the importance of capacity-building processes and allow the development and measurement of population-level outcomes in a realistic timeframe are critical for measuring the success of place-based approaches.