This article provides a model for robust student affairs program assessment using diverse data sources, multiple outcomes, propensity score matching, and cost analysis. Contemporary outcome-based assessment in student affairs requires equity-minded approaches paired with methods that support causal inference and actionable results. As a guide for practitioners, we summarize the approach we used to assess a student success program at a large, research-intensive, Hispanic Serving Institution. We describe the team structure, data sources, and analytical framework for assessing the student journey from admissions through graduation. Essential project management templates such as a sample logic model, data tables, and a project calendar are also included. These tools and strategies can be successfully adapted to meet contemporary assessment needs in student affairs at institutions of all types.