Community Science evaluated MassDevelopment’s Transformative Development Initiative (TDI) after it was first launched in 10 Gateway Cities in 2015. TDI aims to catalyze transformative redevelopment within focused districts in Gateway Cities, helping to accelerate economic growth and to benefit the people and small businesses connected with each district. The evaluation team assessed TDI’s impact, documented TDI’s influence within MassDevelopment (the sponsor organization), and recommended possible program adjustments. The team also recommended opportunities for MassDevelopment to enhance outcome measurement in the future, providing a framework for prioritizing data collection based on the intended audience and its needs. Community Science’s data collection methods included interviews and focus groups with stakeholders in each of the 10 districts and with MassDevelopment staff, site visits to 4 districts, and extensive review of TDI and district documents. Community Science was selected for its national perspective and its expertise with redevelopment and urban planning work. These characteristics equipped the team to make actionable recommendations that TDI has already begun to implement in its second phase.