It is well acknowledged that close collaboration with the customer serves as the lynchpin to ensuring that agile information systems development (ISD) teams produce the right software within mutually agreed targets. In several agile ISD methods, this emphasis on close collaboration is enacted through the role of a designated customer representative (CR). The agile ISD literature has recognized the behaviors in this role to be inherently complementary and contradicting in nature, presenting a challenge to whoever occupies the role and hampering their ability to add value to the project. How do CRs manage these challenges and why do they do so in a particular manner? Unfortunately, there has been little theory to answer these questions. In this research, we explore and theorize about this phenomenon by leveraging role multiplexity as a theoretical lens in making sense of the behavior of CRs in agile ISD. Results suggest that the CR role is multiplex, exhibiting multiple manifestations with different orientations. We develop a theoretical model that articulates the instantiation of these role manifestations and the mechanisms that enable the CR role to remain intact while managing these challenges. The theoretical model highlights the CR role in agile ISD as being dynamic and multi-oriented.