This edited volume discusses the path towards the digital transformation of Georgia from two major viewpoints: First, an economic perspective that includes contributions around economic integration and orientation towards the EU, and an analysis of its implications for a small country like Georgia. Second, various aspects of digital transformation initiatives will be studied from an enterprise and a managerial perspective. In this part, innovative management methodologies are conceptualized such as agile change management and the enterprise transformation cycle to facilitate the shift from the manufacturing and agriculture industry towards an increasing digitalization of companies. These concepts serve as fundamental cornerstones to enable the development of a digital transformation roadmap including the analysis of the potential of establishing a digital hub in Georgia and the Caucasus area. Based on a survey of national and international managers, important HR key performance indicators referring to mobility and digitalization of the workplace are discussed. The impact of pandemic (post-Covid) scenarios for future organizational development as well as large-scale labor migration from East to West is also in focus. The authors present implications for policymakers and business owners as well as top-level executives resulting in a set of recommendations for future actions.