Learning through work is viewed primarily as individuals’ learning and development, albeit often directed towards their workplace purposes and needs. That learning is often linked to changes in their workplaces and occupational practices (i.e. innovations). Both learning and innovations are important for workers’ employability and workplace continuity. Importantly, they often co-occur and are interdependent. Aligning workplace innovations and workers’ learning is, therefore, essential for effective and adaptive workplaces and work practices, and workers’ employability. Hence, it is important to understand these processes further. This chapter reports and discusses the processes and outcomes of learning and innovation in five small- to medium-size enterprises in precision manufacturing and healthcare sectors in Singapore. The practical inquiry comprised interviews and observations. The findings suggest the key factors associated with initiating, enacting and sustaining innovations of different kinds and learning were largely proximal to the workers that comprise zones of development. That is, the disposition and actions of supervisors/managers and co-workers co-create zones of development that permits them to initiate, propose and enact innovations of different kinds. Central to those zones are the workers’ dispositions and actions. These findings indicate the importance of zones of activities and interactions at the workplace in which learning and innovation co-occur.