Developing countries' public health systems struggle with digital health implementation, and reports of low digital health readiness exist within the workforce. This study investigates the perceived digital health readiness of healthcare leaders in operational management to implement digital health tools. A cross-sectional survey using the E-Ready 2.0 scale was used to measure digital health readiness (n = 329) in 11 hospitals in the Western Cape, South Africa (September 2023 – March 2024). Descriptive statistics summarised respondent characteristics and the E-Ready 2.0 subscales: conditions for change at the workplace and among individuals, support and engagement from management, colleagues' readiness, consequences for the status quo and workplace attitudes. Statements scoring 60% or more were considered to have higher readiness. Chi-square and Mann–Whitney U tests were used to examine associations between demographic variables and subscale statements. A total of 143 healthcare leaders responded (56.1% response rate) (n = 114 nurses [79.7%], n = 29 medical doctors [20.3%]). The average age was 46.4 ± 10.0 years. Overall, higher levels of readiness (above 70%) were observed with statements related to workplace attitudes, whereas conditions for change at the workplace and among individuals showed lower readiness (below 50%). Despite significant investment in digital health tools, there remains limited digital health readiness among those responsible for leading these implementations.