Abstract Sustainable business models (SBMs) archetypes have been introduced to develop a common language that can be used to accelerate the development of SBMs in research and practice. The way in which SBMs are triggered by managers or entrepreneurs who act as leader of an organization has not yet been deeply investigated. Accordingly, the works aims to inquire the role of entrepreneurial and managerial leadership style—with a particular focus on servant leadership—in influencing the strategies, the organizational culture and the stakeholders engagement of companies, orienting them toward sustainable business models. After having traced the theoretical background, the empirical research in this chapter helps to shed light on corpo...