The adoption of digital technologies in healthcare, accelerated by the COVID-19 pandemic, requires a well-prepared workforce capable of implementing those technologies. Here, we examine the role and impact of digital fellowships in facilitating digital transformation in healthcare systems. Digital fellowships are structured educational programmes designed to equip healthcare professionals with advanced digital skills. Focusing on UK-based initiatives like the Topol Digital Fellowship and the Fellowship in Clinical AI, we explore their efforts to prepare healthcare leaders for digital and AI adoption. Each fellowship programme provides participants with hands-on experience in digital healthcare projects and fosters interdisciplinary collaboration and post-fellowship support. We discuss how these fellowships contribute to staff retention by diversifying professional experiences and opportunities. We call for increased collaborations between universities, industry, and professional bodies to integrate lessons from digital fellowships into relevant curricula, acknowledging that digital fellowships are just one piece of the puzzle in bridging the digital skills gap in the healthcare workforce.