Recent high-profile incidents have engendered doubts about trust in various firms and have resulted in cyber security becoming a critical risk factor that firms must address. Unsurprisingly, data breaches are currently the biggest concern of CIOs. The goal of this research is to answer the following questions: What are the specific cyber security concerns of the organization’s leaders, and how will those leaders allocate resources to allay those concerns? We intend to use the Technology-Organization-Environment (TOE) Framework through a multiple case study approach. We will be collecting qualitative data through the use of semi-structured interviews of CIOs that are working in various industries in the US Midwest. The goal of this study is to extend the TOE framework to best explain the executive decision process with regards to cyber security.