For vulnerable patient populations, such as children with medical complexity (CMC), the patient journey is fraught with challenges. By providing a range of perspectives including clinicians, a family caregiver, and Human Factors/Ergonomics (HF/E) experts, the present panel will describe the unique opportunities for HF/E to design jointly optimized systems for CMC and their family caregivers, including an explication of some of the specific challenges and complexities related to studying the work of and designing systems for this population. We will also highlight the ways in which HF/E could help in the design of solutions to improve outcomes for families.