As the technology landscape is continually evolving, transitions to newer software are commonplace in higher education. Change is often difficult to navigate, especially when the change that is implemented fundamentally impacts entrenched business processes. In no place is this more evident than when implementing a new system, whether the implementation involves the entire student information system or a new integration with a third-party vendor. This article describes lessons learned through the implementation of a new degree audit and student success application at Carnegie Mellon University and offers best practices for future software implementations.