This chapter focuses on the many changes that advances in technology and the emergence of distance learning education have brought to the work of academics. It therefore links neatly to the previous chapter. It presents the results of a case study, where semi-structured interviews were used to explore the benefits, as well as the challenges, faced by faculty members from a business school at a large university in Cyprus in relation to technological transformation and distance learning education. The participants expressed a high level of satisfaction with the advent of technology and its impact on their work, as well as their willingness to embrace it. They also expressed their overall agreement with the university’s strategic decision to expand its distance-learning (DL) education provision but noted the lack of proper training on the non-technical aspects of DL teaching, the difficulties in terms of achieving student participation and proper interaction, and the issue of how to motivate students who follow DL programmes of study. Other challenges relate to increasing workloads, high levels of bureaucracy and control, and limited resources.