The advancement of digital maturity of healthcare organizations and health systems hinges on the potential of digital tools to empower healthcare professionals. This empowerment extends beyond care delivery to encompass the use of digital technologies for administrative functions, ensuring seamless operations and automated clinical workflows. To achieve a digitally empowered healthcare workforce, building healthcare professionals’ capacity, confidence, and trust in digital tools remains imperative amidst resource constraints faced by healthcare organizations. Integrating data and artificial intelligence within care pathways and clinical management tools offers avenues to enhance healthcare effectiveness and overall improve the health workforce’s performance. As the health workforce evolves, including diverse stakeholders in the digital transformation process becomes paramount to the nurturing of integrated and sustainable digital health ecosystems. This article delineates three user groups—Digital Health Workforce, Health Workforce, and Empowered Citizens—each with defined roles crucial for improved healthcare outcomes and accelerated adoption of digital technologies within clinical practice. Each user group necessitates both technological investment and cultural shift, underlining the need for distinct training and upskilling programs. The authors propose personalized strategies for the further development of the user groups and outline scenarios for fostering workforce-driven digital maturity to ensure healthcare’s resilience in the new demographic era.