Information system (IS) transformation initiatives generally present a wide range of challenges for organizations. These challenges are, however, heightened considerably within organizations that have not traditionally pursued such initiatives. In addition to the many difficulties associated with developing and implementing radical business innovation, inexperienced organizations are simultaneously faced with the need to rapidly acquire the underlying competencies necessary to successfully execute a transformation. This case thus presents a mid-sized, globally oriented organization that is in the early stages of developing its transformative capacity while it undertakes a transformation of its human resources (HR) function. The reader is placed in a position to evaluate the challenges and learning achieved thus far in the process and to offer recommendations aimed at ensuring a successful transformation. Recommendations can also be made in relation to how organizations can foster the growth and development of their transformation competencies.