The goal of our study is to contribute to a better understanding of role conflict, skill expectations, and the value of information technology (IT) security professionals in organizations. Previous literature has focused primarily on the role of information professionals in general but has not evaluated the specific role expectations and skills required by IT security professionals in today’s organizations. In this chapter, we take into consideration the internal and external factors that affect the security infrastructure of an organization and therefore influence the role expectations and skills required by those who are in charge of the security of network infrastructures in organizations. First, we describe the factors discussed in the literature and support them with quotes gathered from interviews conducted with information security professionals in small organizations in Central New York. Then, we present a set of common themes that expand the understanding of this role and finally we provide practical recommendations that would facilitate the management of these professionals within organizations.