The case details the application of a systemic, actor-centered design approach to a strategic process of digital transformation in support of industry/research collaboration in one of the administrative regions of southern Sweden. Project mainstays include regional development of “digital leadership”, the creation of a digital/physical competence center, and a larger plan to connect these mainstays to an already established, extremely successful computing- and entertainment-centered yearly event in the main city in the region. Structured around the initial problem space identification and formalization aspects, the case specifically discusses the competence center, what it should be and what activities it should facilitate. It describes the process followed and the results obtained in the divergent stages of the project by means of the early engagement of different stakeholder groups through workshop activities. Preliminary conclusions are drawn in respect to what challenges currently hinder big-scale processes for the design of complex digital/physical environments and the experiences they enable; the relative solidity of adaptive or transformative approaches versus blended space approaches for digital/physical environments; the role and relative weight of “digital” in the organizational context of digital transformation processes.