Digital transformation has significantly altered workplace dynamics, particularly in regulated sectors like healthcare, where diverse stakeholder competencies and strict legislative frameworks create unique challenges. While existing research has extensively examined digital transformation's technological and strategic aspects, the human dimension—critical to increasing digital service offerings—remains underexplored. The aim of the study is to investigate the interaction between individual and organisational level relationships and the relevance of behavioural aspects and conditions essential for sustaining learning and achieving the strived outcome of increased digital service offerings. This research employs a qualitative approach grounded in dynamic capabilities theory, including interviews and focus group discussions with 31 healthcare sector stakeholders in Germany. A conceptual model is proposed, illustrating how the emerged factors enhance digital service offerings. This study extends the theoretical understanding of dynamic capabilities by redefining sustained learning as a continuous and integrative process critical to digital transformation in healthcare. Practical implications for organisations and policymakers include designing low-threshold learning opportunities, fostering interdisciplinary collaboration, and addressing diverse competency levels. The findings offer actionable insights for navigating digital transformation in resource-constrained and regulated environments, contributing to academic and practical advancements in the field.