A Head Start program in Southwest Georgia wanted to understand whether using Cognitive ToyBox (CTB), an innovative, new assessment tool can improve school readiness. Cognitive ToyBox is the first hybrid observation and game-based assessment platform for early childhood educators. The tool’s unique approach to combining observation and game-based data together enables teachers to save time on assessment and have access to multiple sources of data to understand school readiness. Critically, the automatically generated reports provide tactical information to facilitate instructional scaffolding and individualized student support. Three four-year-old classrooms in the pilot group used Cognitive ToyBox and three four-year-old classrooms in the control group continued using their observation-only assessment tool. Results suggest that CTB scores have a good test-retest reliability (average r=.67, average n=46) and convergent validity with the Brigance® (r=.53, n=44) for preschool aged children. After six months of use, classrooms in the pilot group showed a small but non-significant gain in school readiness compared to the control group. The program also found that, compared to an observation-only approach, a hybrid observation and game-based approach holds promise in helping teachers to individualize instruction on a more frequent basis and ease the transition from Head Start to kindergarten. (author abstract)