The digitalization era has brought about unprecedented challenges for the manufacturing industries, pushing them to deliver solutions that encompass both product and service-related dimensions, known as Product-service Systems. This paper presents a number of lessons learned in the process of integrating the analysis of operational data as decision support in engineering design based on the empirical studies from two Swedish manufacturing companies operating in the construction machinery sector. The paper highlights the need to consider a five-dimensional perspective when collecting and analyzing data, encompassing data from the product, the service, the environment, the infrastructure, and the humans involved. Finally, a conceptual framework for data-driven design automation of Product-service Systems is proposed by leveraging the use of these data, introducing the concept of a Product-Service System Configurator as an enabler of design automation. The implementation of the proposed framework on multiple case studies in different industrial contexts shall be considered as the next step of the research.