This thesis analyzes e-commerce strategies of traditional and digital-first SMEs, using case studies like Librairie Mollat, Midwest Furniture Co., Gymshark, and Tokopedia to explore how typological differences shape digital adoption and competitive outcomes. Traditional SMEs adopt e-commerce reactively, constrained by legacy systems and cultural resistance, while digital-first SMEs leverage agile, platform-native designs for innovation and scalability. Applying Diffusion of Innovation, Technology-Organization-Environment, and Resource-Based View frameworks, it identifies technological hesitation, resource scarcity, and customer-centricity as key strategic themes. The findings reveal a digital maturity gap, with traditional firms needing cultural and infrastructural support to scale, while digital-first firms excel through data-driven innovation. The study advocates tailored policy interventions to enhance SME competitiveness in the digital economy, contributing to academic and practical discourse.