High patient engagement in digital health platforms is critical for effective interventions but is heavily influenced by socioeconomic, demographic, and clinical factors. We describe standardized definitions and an approach to measurement techniques to assess engagement by integrating vendor data with electronic health record data. We describe our strategies for continual program monitoring using automated data integration and dashboards. We describe an approach using both patient interviews and quantitative data to better identify causes for poor engagement and drive the product roadmap and future improvement. Our team has implemented digital health programs focused on remote patient monitoring and electronic patient-reported outcomes, encompassing a broad set of patients, including programs in lung transplant, inflammatory bowel disease, hypertension, orthopedic surgery, and living organ donors.