Multiple companies and organizations use Enterprise Systems daily. Best practices and critical success factors are frequently used both in the literature and by vendors that develop and sell Enterprise Systems. As organizations and companies are unique in different aspects, the challenges that mid-sized companies face in the procurement of Enterprise Systems and the decisions that lead up to the final choice of vendor requires knowledge and resources. This study is a single case study based on company A and their current procurement phase. Data has been gathered through interviews with employees in managerial positions and a procurement consultant.Results are then compared with current available theory in Enterprise Systems and decision making. The challenges for Company A and their current procurement process are compared towards the consultant’s point of view. The discussion changes towards beneficial structures are discussed. This paper will introduce Company A and their processes together with suggestions on how to improve the process, but the suggestions should be seen as theoretical due to low quantitative validity.