This paper is a case study of a user experience based project in an enterprise setting at Cisco systems, Bangalore to improve an agent desktop experience through HCD methodologies in an Agile software development setting. The core experience revolved around agents’ interactions with customers to solve their queries and resolve them. The product, already existing in the market was dated and needed a user experience refresh. The product, already existing in the market was facing a crisis because customers were not using them actively. The design team was brought in to help design the upcoming features in a User-centered way. Intensive user-driven research using the principles of systems-oriented and interaction-design were applied and the team identified core personas, made task flows, collected customer feedback, conducted user interviews, customer validations and made design concepts, recommendations and approaches. Pursuing this path, the methodologies led to some changes - design, technical and operational. This case study explores the journey and underlying issues of what challenges were faced and lessons learned by the user experience design team in an enterprise setting.