Developing the digital health environment for the future is an important and prioritized initiative to meet increasing demands and requirements for high-quality healthcare. The digital transformation of healthcare not only entails changes in the IT environment but also affects the healthcare professionals’ daily clinical work, as it includes changes that require learning and the development of new working methods. The challenges are thus both complex and sociotechnical, which calls for holistic approaches and a better understanding of existing practices and new competencies required in response to current changes associated with digitalization. In this context, workplace learning plays a vital role. This paper draws from initial experiences of a digitalization initiative at two hospitals in Sweden, which partly focuses on the management and organization of digital transformation. By studying the development, implementation, and use of digital technologies from a learning perspective, the main focus is to contribute to better knowledge about how to lead and organize workplace learning for healthcare professionals, which also benefits the patients. The aim is to identify key activities associated with learning in healthcare digital transformation. Hence, we propose a conceptual model that illustrates and exemplifies activities and roles related to learning through digital change. In conclusion, we argue that a better understanding is needed of i) how management and organization can facilitate change in working methods and related processes, and ii) how learning in everyday work can be integrated with digital transformation in order to achieve the full potential of digitalization. © 2022 Copyright for this paper by its authors.