The financial crisis of the last decade has left many financial institutions with limited personnel and equipment resources. Thus, the IT departments of these institutions are being asked to explore novel approaches to resolve these constraints in a cost-effective and efficient manner. The goal of this paper is to measure the impact of modern enabling technologies, such as virtualization, in the process of replacing legacy infrastructures. This paper proposes an IT services upgrade plan approach for an organization by using modern technologies. For this purpose, research took place in an operating financial institution, which required a significant upgrade of both its service-level and its hardware infrastructure. A virtualization implementation and deployment assessment for the entire infrastructure was conducted and the resulting consolidated data are presented and analysed. The paper concludes with a five-year financial-based evaluation of the proposed approach with respect to the projection of expenditures, the return of investment and profitability.