During the past decades, technology quickly took a predominant role within the architecture of organizations and enterprises of all sizes and purposes. From public relations to business functions, information systems are employed to simplify tasks and optimize workloads. However, with great benefits also come significant disadvantages: exposure to cyber threats and cyber risk. In a world where cyber attacks could easily disrupt companies and damage stakeholders, the precise evaluation of the cyber risk factor is crucial, both for companies desiring to mitigate their risk and for insurance providers. The risk analysis process is costly and time-consuming, requiring particular efforts for information gathering and the consequent processing of it.