In order to realize the digital society in which no one is left behind, we have been engaged in architectural design and data standardization for digitalization of social systems, promotion of digital transformation (DX), cyber security in the era of cyber-physical integration, and digital workforce development. Realizing the vision of the digital society requires both security measures and DX promotion. We have been conducting various examinations such as information security management and operating the registered information security specialist system for the development and evaluation of security workforce. The number of applicants for the information security management examination has increased more than three times since the computer-based testing system was introduced in 2020. We will conduct proof testing of the internet-based testing in 2022. To promote companies’ DX initiatives, we developed WISDOM-DX, a system that leverages a QA system based on Web information that automatically evaluates the DX initiatives of companies without manual DX survey. WISDOM-DX was tested by ranking 464 companies including 48 distinguished companies selected by human experts of DX Stocks 2021. The precision of the top 48 companies ranked with WISDOM-DX was 56.3%, and 91.7% of them had a certain level of achievements for their DX initiatives.