The role of a chief operating officer (COO) is one with which many club football fans may be unfamiliar. Indeed, many of even the most devoted fans may be unable to name who their club’s COO was or currently is. Typically, the executive director occupying the position is not exposed to external scrutiny from the media, club supporters or indeed organisational scholars, and as a result goes mostly unnoticed. This is somewhat surprising, given that the role encompasses a variety of strategic club responsibilities, which lead to it being identified as one of the most crucial and challenging leadership positions in any business operational context. This chapter explores the multifaceted role and range of responsibilities of the COO. The focus in the first half of the chapter is upon exploring the leadership and management of clubs’ internal operational requirements. The second half of the chapter affords privileged access to a high-ranking EPL COO. The interview provides insight into the complex reputational and compliance risks and the operational inefficiencies for which a COO is held accountable.