This chapter discusses findings from three case studies of pioneering smaller medium-sized municipalities in the field of digitalization. It describes the governance of digital policy and its explanatory factors from a comparative perspective, focusing on commonalities and differences across cases; it then presents a typology of organizational structures for the governance of digital policy and puts forward a model of a self-reinforcing positive feedback loop to explain dynamics of change over time. Across pioneering municipalities, a shared trajectory of growth of the policy field can be observed over time. There is a defined trend toward increasing institutionalization of the policy field, growth in personnel capacity, expanding policy scopes from e-government to both e-government and e-participation, and larger and more diverse actor constellations. However, the configuration of the growth trajectory is case-specific. Significant variation in organizational structures and in (de)centralization can be observed over time and across cases. Both modes of radical and incremental change are present. Certain factors have an influence on the governance of digital policy: political support of the mayor, the presence of digital champions, pilot projects and external grants, changes to the legal framework, and the financial situation of the municipality help explain the trajectories of growth. The interaction of explanatory factors configures a historical institutionalist positive feedback loop. A snowball effect in which a municipality’s previous trajectory in digital policy, the existence of engaged individuals and institutions for the governance of digital policy, and political support make the acquisition of funds easier, promoting institutionalization, more personnel resources being allocated to the governance of digital policy, and more scope for growth in terms of tasks and objectives. The typology of organizational structures for the governance of digital policy typifies the variance in smaller medium-sized municipalities according to institutionalization, capacity, and cross-sectional or line organization. Interdepartmental digitalization officers, interdepartmental digitalization teams, digitalization officers, digitalization departments, de facto digitalization officers, and IT departments can all be found in charge of digitalization at this size.