Design is increasingly deployed by governments and cities to address social and policy-related problems and to develop public services and organizations towards more citizen centeredness. Design activities in complex and hierarchic public organizations easily meet challenges, making their impact elusive. More knowledge is needed on the organizational requisites of public sector design. This article provides an empirical analysis of the challenges and opportunities of embedding design in a large public organization, as perceived by fourteen city officials. The case organization, City of Helsinki, has been a pioneer in using design at the strategic level and using it widely in its organization. The results show that differences between the design field and the public sector not only offer complementarities but also create friction in the practical utilization of design. Moreover, the discontinuity and fragmentation of design activities, the highly variable maturity levels within the city organization, the integration of design into projects, and more encompassing leadership, change management, and implementation of the results of design projects were seen as future development areas.