Digital transformation and servitization have been merging in a coalescing paradigm called Digital Servitization, changing not only companies’ business model but also their portfolio and thus their business. This hybrid paradigm is increasingly overwhelming manufacturing companies, compelling them to change their business model and provide more complex solutions to survive. Indeed, first a business model shift is needed (bringing to cope with organizational/managerial aspects), and then a suitable new technology stack has to be implemented. In the extant literature it is not clear how companies can define which are the improvements to implement on Smart Connected PSSs. These modifications on the physical products, if flanked by a concurrent definition and structuring of data requirement on the database on the cloud, would also lead to a better comprehension of the solution functioning, enabling to know which are the causes leading to breakdowns and performance and quality losses during the use phase. To address this, the paper proposes a method combining the Failure Mode and Effect Analysis with the Overall Equipment Effectiveness framework.