A constant challenge facing university faculty and academics is determining how innovative and authentic elements, based on constructivist philosophy, can be manifested effectively in online learning settings. In this article, we describe an educational technology postgraduate course on evaluation that incorporated a scenario whereby assessable tasks were grounded within the context of a fictitious consultancy company. The scenario was driven by the use of a fictitious character a remote Chief Executive Office (CEO) and the reconfiguration of the teacher as a company recruited Academic Advisor. Characters were used as a motivational device to drive the online activity for the course, which was delivered completely online. The evaluation findings highlighted that whilst the company scenario and use of character did provide an authentic learning experience for most students, its use required considerable support and scaffolding in order to maximise its potential to facilitate an engaging and authentic learning environment. This article describes the rationale for the course redesign, explains the approach taken to evaluate the effectiveness of its implementation and presents the findings of the evaluation.