Current managerial practices and social trends are incentivizing an increase in citizen participation and government operational transparency and accountability. As a consequence, small to medium size cities have new opportunities for delivering services to their citizens in a more effective and efficient manner. However, in many cases, the technology capabilities of these cities and their IT staffing are not adequate. Starting at the top, most small-to-medium size cities do not have a Chief Information Officer (CIO). Instead, they have appointed officials with a wide variety of titles ranging from IT Director, IS Manager to IT Specialist among others. These officials face the problem of building operational capabilities at the same time that they develop a strategic vision for their organizations. In this paper, we look at the perceptions of local-level officials responsible for the operation of IT across New York State, about their own role and challenges in this transition from an operational to a strategic focus. Our results suggest that giving IT leadership a broader role and higher responsibilities could result in value for both government and citizens.