This whitepaper details a Product Owner's experience with upgrading a traditional IT Service Management (ITSM) system and explores the benefits of Atlassian's Jira Service Management as an alternative. Traditional ITSM upgrades are often complex, time-consuming, and disruptive. In contrast, Jira Service Management offers flexibility, easy configuration, and incorporates Agile methodology. It provides continuous improvement through frequent feature releases and a loosely-coupled architecture, making upgrades more efficient and less disruptive. The whitepaper emphasizes the advantages of Jira Service Management in enhancing ITSM processes.