Advances in artificial intelligence and data analytics have unlocked new opportunities for progress in critical areas within the maritime domain. Over the past year, the U.S. Navy has initiated an Operator Decision Aid pilot project to apply rules-based navigation algorithms developed by the U.S. Defense Advanced Research Projects Agency (DARPA) and Office of Naval Research (ONR) to provide real-time recommendations to watch-standing teams on the Bridge and in the Combat Information Center. Recognizing the complexity inherent in the employment of artificial intelligence-based solutions, this paper will apply a multifactor framework developed by Crawford and Pollack (2004) to evaluate influential aspects of the project required to drive change, embrace complexity, and institute a culture of learning.