The thesis provides a longitudinal empirical analysis of the processes of organizational co-evolution enabled by digital transformation in the cultural heritage sector in Italy. In particular, the thesis looks at changes in the performance of the most important Italian cultural organizations by analyzing - in historical series - the technological, organizational and strategic changes pursued from 2011 to 2019. To conduct this analysis a unique dataset was used, built ad-hoc for this study that aggregates ISTAT and Mibact data from 2011 to 2019. The thesis aims to understand how cultural organizations need to configure their activities and enabling technologies, to achieve a sustainable competitive advantage in an environment characterized by strong organizational complexity.