This study investigated a digital reform initiative, rated excellent by the government, of one higher education institution (HEI) in an Arab State in the Gulf. The focus of the study was to develop a digital typology, while exploring the leadership attributes that characterized the core leadership team, as they accomplished the migration towards a digital culture in one year, within a context where faculty members showed resistance against digitalization. The study was conducted immediately after the implementation of the initiative that took place over the course of one year, just before the COVID-19 pandemic. Semi-structured interviews were conducted with all the six key individuals in the leadership team who led this initiative. Data was analyzed using content-based analysis. Findings of the study were used to synthesize a 5D typology for digital leadership attributes: (1) Digital competence; (2) Digital culture; (3) Digital Differentiation; (4) Digital governance; and (5) Digital advocacy. The paper provides in depth discussion how these attributes supported the adaptive ability of a Higher Education Institution towards accepting digitalization.