The development and diffusion of digital technologies (especially those supporting communication, collaboration and social networking), along with the pervasive dissemination of powerful and easy-to-use mobile devices, may encourage organisations to implement Smart Working (SW). The previous research suggests that an effective SW implementation is enabled by the availability of a certain set of resources, namely advanced ICT infrastructure and digital technologies, employees’ digital skills and acceptance, and a trust-based organizational culture and managerial style. Despite this, the existing studies neither empirically determine the role of enabling resources for an effective SW implementation nor explain the interplay of different SW enablers in the improvement of organization performance. This study investigates through an empirical study the relationship between the SW enabling resources and the organization performance. Furthermore, this study aims at analysing the mediating role of digital leadership on the relationship between the SW enabling resources and organization performance.