The digital economy is now upon us, providing new customer-centric business models fostered during the digital transformation of Industry 5.0. Social networks, mobile applications, data analytics, cloud dependency, and the (IoT) Internet of Things were just vehicles for change. Swept up in this rush for automated business operations is awareness of balancing network complexity and personalizing information measurement systems. This chapter takes a five-pronged approach to situate where the concept of personalized measurement design fits within Industry 5.0. The first section explains how digital transformation has merged multidisciplinary specializations. The second section deals with the preparations for personalized measurement design to enhance the flexibility of online assessment practice. The third section shows how social science knowledge society opens an Industry 5.0 pathway to achieve fully automated human-computer interaction (HCI). The fourth section is about designing flexible online assessments. The final section discusses the next generation of learning analytics.