The three cases provide a longitudinal account of the transformation of the Human Resource (HR) division of Mahindra’s Automotive and Farm Equipment Sector (AFS). An aspirational nudge from the Managing Director about the need for a more strategic HR role triggered the transformation exercise. The follow-up diagnostic study revealed significant gaps in the readiness of the HR division for the future. The redesigned HR organisation with three pillars of Shared Services, HR Business Partners, and Centre of Excellence turned out to be quite successful. The efficiency improved, and HR gained a reputation for being a strategic partner to the business. With a high degree of standardised processes, the HR organisation seemed ready for digitisation. The three cases have been written in a way so as to provide the readers a detailed description of the diagnostic process in Case A, the restructuring and change process in Case B, and the impact of the transformation exercise in Case C.