Background: The COVID-19 pandemic has sped up digital health transformation across the health sectors to enable innovative health service delivery. Such transformation relies on competent managers with the capacity to lead and manage. However, the health system has not adopted a holistic approach in addressing the health management workforce development needs, with many hurdles to overcome. The objectives of this paper are to present the findings of a three-step approach in understanding the current hurdles in developing a health management workforce that can enable and maximise the benefits of digital health transformation, and to explore ways of overcoming such hurdles. Methods: A three-step, systematic approach was undertaken, including an Australian digital health policy documentary analysis, an Australian health service management postgraduate program analysis, and a scoping review of international literatures. Results: The main findings will guide the formulation of strategies in developing a digitally enabled health management workforce in the digital health era. Conclusions: With the ever-changing landscape of digital health, being able to lead and manage in times of system transformation requires a holistic approach to develop the necessary health management workforce capabilities and system-wide capacity. The evidence would support that this can be achieved with the required system, policy, educational and professional organizational enablers, which drive a digital health focused approach across all the healthcare sectors, in a coordinated and contextual manner.