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In this dissertation, we evaluate the roles senior management teams and individual middle managers play in realizing the performance benefits of entrepreneurial orientations. We investigate the role of senior management teams by focusing on a sample of 9.000 firms in the Netherlands. The first study focuses on antecedents of entrepreneurial orientation, i.e. internal and external knowledge acquisition of senior management teams. We find that both internal and external knowledge acquisition are important and that a premium in terms of the entrepreneurial orientation of the firm may be obtained by simultaneously sourcing for both types of knowledge. Our second study presents a model for top management teams aiming to enhance the performance benefits of the entrepreneurial orientation of the firm. We investigate team attributes such as team heterogeneity and shared vision and find some compelling results with respect to their context specific applicability for leveraging the entrepreneurial orientation of the firm. Our final study, based within the European branch of a single firm operating at the intersection of hardware, software and IT consulting, examines the individual entrepreneurial orientation of middle managers and subsequent performance benefits. We find that strong network ties of relatively higher placed middle managers are instrumental for realizing the inherent value of entrepreneurial orientation. Together, our results emphasize the performance benefits that may be obtained if the entrepreneurial orientation of organizations and individuals is appropriately managed. Attention for knowledge acquisition, team composition, the environmental context as well as network ties and the hierarchical position of individual managers represent essential aspects of effective management of entrepreneurial orientations.