This study examines how technology-mediated market entry strategies contribute to competitive advantage among small and medium enterprises (SMEs) in Sub-Saharan Africa. Drawing on the Resource-Based View and the Dynamic Capabilities Framework, the research employs a quantitative cross-sectional survey design with 412 SME owners and managers drawn from Nigeria, Kenya, Ghana, and Cameroon, stratified across three sectors: retail and trade, manufacturing, and services and ICT. Data were collected via a structured questionnaire and analysed using multiple regression, one-way ANOVA with Tukey HSD post-hoc tests, and moderated regression analysis. Three principal findings emerge. First, digital technology adoption and technology-mediated market entry strategies jointly explain 56.0% of the variance in competitive advantage (F(2,409) = 260.5, p < .001), confirming that technology is a significant enabler of SME competitiveness in the region. Second, significant cross-sectoral differences in digital adoption exist (F(2,409) = 18.74, p < .001, eta² = .084), with services and ICT firms demonstrating substantially higher adoption than retail or manufacturing SMEs. Third, institutional and infrastructural barriers significantly moderate the relationship between digital strategy adoption and competitive advantage (Delta R² = .026), attenuating the benefits of digital investment in environments with weak regulatory and connectivity infrastructure. Social media marketing (87.6%), mobile payment platforms (80.1%), and digital advertising (70.1%) are the most widely deployed tools, while AI-assisted analytics remain nascent at 27.9% adoption across the sample. The findings contribute to the growing body of literature on digital transformation in emerging markets and carry practical implications for SME owners, policymakers, and development finance institutions operating in Sub-Saharan Africa.