The interaction between static and dynamic facets in organizational ambidexterity produces “change” energy for the organization. The purpose of the research therefore is to examine the predicting role of organizational ambidexterity for entrepreneurial orientation and idiosyncratic deals (i-deals). The moderating role of corporate social responsibility (CSR) in the effect of organizational ambidexterity on entrepreneurial orientation was also investigated. The cross-sectional data for SEM-based analysis were garnered from 427 supervisor-subordinate dyads from software companies in Vietnam business setting. The research findings confirmed the positive relationship between organizational ambidexterity and entrepreneurial orientation, which was moderated by CSR. Entrepreneurial orientation was also found as a strong predictor of i-deals.