ICH is the evaluator for the College Success Initiative (CSI), a partnership among several Cambridge organizations, the Cambridge Public Schools, and local colleges and universities to provide coaching and other supports to low-income students to guide their transition into and completion of post-secondary programs. ICH led CSI through the process of creating a logic model, identifying key program outcomes, and developing a multi-year evaluation plan to measure progress towards those outcomes. The mixed-methods evaluation plan includes quantitative data collection from surveys and secondary data sources as well as qualitative collection through interviews of CSI students. To date, we have interviewed 14 students. Evaluation findings have helped CSI further understand the needs of its target population and improve its coaching structure and supports accordingly.