This study examines how digital transformation is reshaping women’s entrepreneurship in Africa through a comparative lens on Senegal and Cameroon. Using a qualitative design with 15 semi-structured interviews, we show that digital technologies expand women-led firms by opening new markets, improving managerial practices, and enhancing visibility. Yet these opportunities remain contingent on institutional frameworks, mediated by social and professional networks, and moderated by sociocultural norms. Findings indicate that Senegalese entrepreneurs benefit more from incubators and public programs, whereas Cameroonian entrepreneurs rely primarily on private and informal networks. We develop a five-part typology of digital strategies—social-media expansion, crowdfunding/pre-sales, organizational flexibility, digital formalization, and platform partnerships—to account for differentiated trajectories. Theoretically, three propositions underscore the centrality of context, networks, and norms in shaping digital adoption. We conclude with operational recommendations for policymakers: women-focused incubators, targeted digital training, and tailored financing mechanisms.