In 2012, the United States Department of Education announced the Race to the Top-District grants. One joint award was made to two large educational cooperatives in the same state that together represented 111 mostly rural schools in 22 districts. One of the grant's identified four essential projects was the implementation of personalized learning. This article describes how the grant's external evaluation team worked with grantee leadership and school districts to operationalize personalized learning and then develop and implement Innovation Configuration Maps to measure school-level personalized learning environments. Developmental steps, adoption processes, and preliminary school-level results are reported.