The successful implementation of an enterprise system requires training and end users in the new systems and procedures. There has been no research reporting a relationship between Domain Expertise (DE) and the successful implementation of an enterprise system. This study sought to begin filling this knowledge gap by exploring the relationship between DE, technical proficiency, training outcomes, and perceived training effectiveness for a new enterprise system, specifically a Case Management System (CMS) in a small and medium enterprise (SME). The research examines different subjects of technical expertise including skills, abilities, and knowledge to increase professional acceptance in the high domain of expertise field. In order to understand the complex nature of expertise and the significant impact, an exploratory approach is undertaken. Purposive sampling was utilized to select the 88 respondents to participate in the research, in which the role of domain expertise and technical expertise is explored. Based upon analysis, research showed the relevance of domain expertise and technical expertise in the deployment of successful case management systems. The results contributed to literature by showing that how training influences soft skills such as tacit knowledge on organizational culture and potential clients, deliver best solutions to the project management. Meanwhile, the outcomes provided significant traits on perceived training effectiveness, which drive increase in knowledge, practical implication, and quality of project delivered, presentation skills, communication and problem-solving abilities. The study also contributed to the literature in terms of defining how technical and domain expertise not only effect the outcomes of case management systems but also develop greater coordination for dealing the intricacies, project difficulties, and task-related complexities.