This chapter addresses how school leaders can support teachers’ professional learning and technology integration through a learning design perspective. Through this perspective, teachers engage in sensemaking to enact policy through teaching and learning. This can afford an authentic and contextualized approach to teachers’ professional learning. To do this it is necessary for school leaders to create a culture of learning and experimentation. School leaders can do this through fostering teachers’ engagement in contemporary professional learning, such as developing personal learning networks and communities. These can be online or face-to-face in local schools, or a mixture of the two, formal or informal, and structured or unstructured. The chapter highlights that professional learning should be flexible and personalized to teachers’ contexts. This is increasingly possible as teachers have access to diverse networks and communities, which support engagement with a wide range of professionals, resources, and experiences that may not be available in local schools. The chapter concludes with recommendations on how school leaders can employ a learning design perspective to create this includes opportunities for teachers to make sense of technology integration and experiment and continuously learn to support digital technology use in their school context.