Current waves of digital innovations are continuously accelerating the pace and the scope of change that chief information officers (CIOs) must manage. To remain relevant and effective in their leadership roles, CIOs must be effective change agents. They enjoy longer tenure, enabling them to complete their transformational journeys more effectively. However, the question of whether these change agents can be equally effective in the beginning and at the end of their mandate has largely been ignored in the IS literature. To fill this gap, this paper examines how and why the role of change agent evolves as CIOs progress in their tenure in office. Drawing from the management and the IS literature and the results of a revelatory case study of the CIOs of a large university system in the US, this paper proposes a three-phase model describing what combination of change agentry models is followed by CIOs as they progress in their tenure and why. The combination of change agentry models that CIOs tend to follow during their time in office is explained by the patterns of evolution of five key characteristics: commitment to a paradigm, task knowledge, information diversity, task interest, and power and influence.