This qualitative study examined the changing roles and requirements for deans as educational leaders at Canada’s post-secondary institutions with a service system perspective. Communicating these changes was the focus of this study, with the role of fundraising being placed under a microscope for closer analysis. A content analysis approach was used to capture, code and analyze 248 job advertisements for the position of dean in Canada from 1970 to 2011. The findings show that in many cases the role of post-secondary deans as advertised in recruitment efforts is evolving to reflect the nature of service systems. With respect to the role of fundraising, only 23 job advertisements mention fundraising as either a duty that the dean would perform or as pre-requisite experience. This research points to a need to focus our communication to future educational leaders on the skills that will enable them to excel in a dynamic environment thus improving our nation’s educational offerings.