This chapter reflects on the early career experiences of a healthcare clinician-cum-manager. It describes these influences on the emerging professional interests in work design, the persona of a work design strategist, and the implications of design in healthcare settings. A vision is shared about the creation of a new role in healthcare organisations: the chief work design strategist, influenced by positive psychology to foster innovation. The role is considered as a contemporary method to advance design strategy and integrate business and service strategies. The role is framed as one that will shape design capacity, literacy, and capability; and one that will manage the relationships with conventional design project partners. The inspiration for this vision centres on a belief that regenerative design practice can lead to more sustainable healthcare service delivery.