The work addresses attention to the leadership attributes that allow managers and entrepreneurs to develop authentic CSR-oriented strategies and foster sustainability. After tracing the theoretical framework, the work presents the empirical analysis based on a qualitative approach and a case-study method relative to an Italian company − Geico Spa whose traits of excellence are relative to both the business and the leadership model.Findings point out that the leadership style leads to a business model that allows people inside and outside the company to flourish and the company to grow across all dimensions (economic, financial, competitive, social, environmental and ethical). Moreover, the analysis reveals that what authentically drives CSR strategies and animates the organization to achieve a sustainable development is a leadership style that lies on a passion for the good of the company pursued in harmony with that of all its internal and external interlocutors and its surrounding environment. The work has both scientific and managerial implications. On the one hand, it contributes to shed light on the relationship between intrinsic motivation, charismatic, servant and transforming leadership and authentic CSR. On the other hand, the study points out specific virtues that enable virtuous competencies for enhancing CSR and sustainability that can be developed through educational and professional practices, thus opening new trajectories for a fruitful convergence of theory and practice.