Many organizations are migrating their old, on-premises Human Capital Management (HCM) systems to newer, cloud-based HCM systems as part of their overall digital transformation. An example of this migration occurring in the higher education and public sectors would be the migration from Oracle PeopleSoft HCM to Oracle Cloud HCM. This paper will examine the various strategies utilized by organizations when migrating to cloud HCM systems, the common technical and organizational challenges they face in the process, and most importantly, identify the best practices for achieving long-term success. The paper will cite anonymized case studies of organizations making the migration to Cloud HCM systems with the following results: one University reported that after migrating to Oracle Cloud HCM they reduced their payroll cycle time from 10 days to approximately 2 days (approximately 85% reduction); a County reported they reduced their hiring timeframe from approximately 140 days to 45 days (approximately 68% reduction) after migrating to Oracle Cloud HCM. These results illustrate that implementing cloud HCM systems will increase the operational efficiency, provide better user experiences, and allow for greater regulatory compliance than legacy HCM applications. This paper provides a roadmap for organizations that are currently implementing a cloud migration strategy for their HR processes and systems. It anticipates that future innovations within cloud HCM platforms will come from the increasing use of automation to complete routine business tasks, utilizing predictive workforce analytics, as well as enhanced system integrations between multiple ERP solutions. This study confirms that cloud HCM migrations, when treated as strategic transformations, result in substantial operational and compliance benefits. Institutions adopting cloud-native HCM solutions gain additional advantages when migrations are approached as cross-functional transformations.