In the last years it has been widely recognized the great relevance to identify and manage leadership traits in agile and remote working organizational settings. Entrepreneurs and top managers are increasingly playing a fundamental role in addressing the organizational changes determined by digital transformation and the adoption of new ways of working by rethinking consolidated structures and processes, fostering a culture of innovation and leading HR to adopt new mindsets, knowledge, and attitudes to thrive under continuous change and challenges. Despite this importance and the attention recently paid by academic and managerial studies trying to shed light on these issues, a full and shared setting of findings, insights and managerial and policy guidelines about the new styles of leadership and the required characteristics for a leader best suited the creation and the management of agile and remote working teams is still limited and also results are presented often in a jeopardized way. This paper analysed the main results of a scoping literature review on the main trends regarding challenges and opportunities for leadership in agile and remote working and the characteristics and skills required to entrepreneurs and managers to lead the organization in remote working contexts. The theoretical insights have been then examined and tested in Basilicata, a rural region in the southern Italy. In such a prospect, the research explored whether and how companies headquartered in Basilicata adopt remote working practices and analysed the leadership traits essential for their successful implementation.