Several manufacturing companies are coping with the need to change their business model, being compelled to provide smart, connected and servitized solutions to their customers to survive in the market. A strategic trigger and catalyst of such a transition is represented by digital technologies. Embedded on physical products, digital technologies enable knowledge-based services capable not only of monitoring but also of controlling and optimize, sometimes even at an autonomous level, the system provided to the customer. However, several hurdles (categorized in technical/technological, organizational, human resources-related, and customer-related) can be met along the digital servitization path. It is still not clear what should be implemented in a company internally realizing the need of implementing the digital servitization transition. This paper has the aim of conducting a strategic analysis to understand how to initiate to the digital servitization phenomenon a company producing machineries for the decoration of plastic objects and containers.