This article describes the evolution of an academic professional development program, related to the use of WebCT in teaching programs, and discusses the challenges that have arisen for the members of the staff development team since the original implementation of the program. The training program begins with face-to-face workshops, covering pedagogical issues as well as technical and practical aspects of the software. The workshop series has matured in its format and content in response to staff requirements and demands, as well as software upgrades. This article describes the ongoing evolution of the workshop program, and discusses the changes the staff developer role has undergone, in relation to strategic provision of support for academic staff and contributions to organisational policy development.