This intervention study investigates the influence of digital transformation on women’s leadership and governance within the Senegalese retail sector. Although digitalisation is a key economic driver, its specific impact on gendered power dynamics in enterprise management remains under-researched in West Africa. Addressing this gap, the research employed a longitudinal, mixed-methods design centred on a structured digital literacy and strategic management training programme. This intervention was delivered to women retail proprietors in Dakar and Thiès from 2022 to 2024. Data were collected through pre- and post-intervention surveys and in-depth interviews to measure changes in leadership practices, decision-making autonomy, and governance structures. Results demonstrate that the targeted intervention significantly enhanced participants’ perceived leadership efficacy and promoted more inclusive, data-informed governance models. Concurrently, the study identified persistent structural constraints, notably limited access to finance and entrenched socio-cultural norms, which inhibited the full realisation of transformational leadership. The research makes an empirical contribution to feminist business scholarship in Africa, illustrating that context-specific digital capacity-building can act as a catalyst for advancing women’s leadership. It concludes that for digital transformation to foster equitable outcomes, it must be integrated with concerted efforts to address the systemic barriers facing women entrepreneurs.