The evolution of cloud computing (CC) over the past few years is certainly one of the greatest advancements in the history of computing. However, for this technology to reach its potential there must be a clear understanding of the issues involved in its adoption. The purpose of this exploratory case study is to build an evaluation model that takes into account aspects such as the advantages, challenges and obstacles of adopting CC. To assess the feasibility and usefulness of such model, an Academic Control System (ACS) from an International School was analyzed. Such analysis enabled the development of recommendations, the provision of inputs and the suggestion of actions necessary to launch the ACS as a cloud service. The model revealed challenges regarding governance, human resources (HR) management, project management and organizational culture to deal with innovations and changes. Such challenges shall be taken into account in the cloud strategy. Also, security issues, business models, technical capacity, performance, service level agreements (SLA) are obstacles that organizations willing to provide such services must face. According to the model, the recommendations to overcome such challenges and obstacles include HR management good practices, risk management processes and well-defined decision making instances.