We developed the WISDOM-DX Recommendation System by extracting digital transformation (DX) activities of companies from web information and using generative AI summarization. This system recommends Manabi DX learning contents for DX talent development to learners based on the DX activity status and levels of their companies. The WISDOM-DX Recommendation System first extracts various DX activities for each company from web information and evaluates the activity levels. The extracted activities are then summarized by generative AI to generate a company’s DX summary. The system calculates the similarity between this DX summary and the Manabi DX learning contents. Based on this similarity and the consistency between the DX activity level and the Manabi DX contents level, the system determines the matching degree and recommends learning contents to DX promoters of each company. Using this system, we recommended 10 Manabi DX learning contents from the 732 available in Manabi DX to 63 companies. Sixty-one companies (97%) expressed interest in any of the ten recommended items, and 41 companies (65%) showed interest in five or more items. Future tasks include improving the system with Manabi DX learners' personal histories, providing information to content providers of Manabi DX, and enhancing the digital human talent development platform based on the system.