In an environment where technologies continuously evolve, we must seek to understand how sport professionals evaluate innovation. The purpose of this study is to identify critical factors influencing sport organization leaders’ decisions to adopt a technological innovation as the best strategy to gain efficiencies. We explore the factors influencing sport managers’ evaluation of technological innovations— prior conditions (i.e., need identification and individual innovativeness), perceived characteristics of the technology (i.e., relative advantage, compatibility, complexity, trialability, and observability), and situational constructs (i.e., trust and cost)— and the effect they have on leaders’ decisions to adopt or reject a given tool. The context of this study was high school athletic directors (N = 628) and their decision to adopt or reject digital ticketing as the best course of action for securing revenue and serving their event attendees. From a theoretical perspective, we extend the conceptual model proposed by Rogers’ (2003) diffusion of innovations theory to include situational constructs, which provide future explorations of technology adoption with the flexibility to account for specific complexities of the situation considered within a wide range of sport settings. From a managerial standpoint, the insights are valuable to companies and professionals developing and promoting innovative technologies.