This article reports on a study of the career orientations of the academic staff complement of a tertiary education institution that underwent an intensive organisational transformation process. Career orientation profiles were obtained from a sample of academic staff at the beginning of the organisational change process and five tears later the study was replicated. One primary transformational objective of the organisation was the requirement of staff to engage in entrepreneurial projects to generate a variety of alternative income streams. The focus of this article falls on the assessment of the impact of the changing organisational demands and situational motivational factors with regard to the prevalence of entrepreneurial orientations amongst academic staff. Results indicate a change in orientation profiles linked to entrepreneurial behaviour, but the evidence regarding the direct impact of environmental factors on such profile changes was inconclusive. Implications for higher education institutions are discussed. (Contains 7 tables.)