The Topol Programme for Digital Fellowships in Healthcare is a flagship national programme for digital health aspirants in England. This programme is heavily over-subscribed with applicants, representing a cross section of healthcare professionals interested in a future digital health career. The aim this study was to identify motivations, priorities and experiences of these applicants. Systematic qualitative and semi-quantitative analysis of an entire cohort of anonymised applications to the 2021 Topol Programme for Digital Fellowships in Healthcare were performed. Two-hundred and eighty applications were received from diverse healthcare professional roles. There were limited applications from mental health or social care sectors. Most applicants reported good organisational support from their employers, but limited interaction with senior digital leaders within their organisations. Relatively limited consideration of health inequalities or engagement with industry was noted. Women were statistically significantly more likely to consider health inequality/inequity implications in their applications. The analysis offers an insight into motivations, priorities and experiences of the next generation of digital health leaders. There is a need to link aspirants with local digital leaders and to support broader consideration of health inequalities. Supporting such needs and gaps is expected to further help meet recommendations proposed in The Topol Review and contribute to optimising the skills of the future digital health workforce.