Digital transformation among small and medium enterprises (SMEs) in developing countries is limited by a persistent gap between prevailing adoption frameworks and the sociocultural realities of target populations. Frameworks such as the Technology Acceptance Model (TAM), the Technology-Organization-Environment (TOE) framework, UTAUT, and IDT were originally developed for industrialized contexts and do not adequately account for the cultural factors influencing adoption behavior in structurally distinct environments. A systematic mapping of 256 articles revealed that only 14 consider cultural behavior as a variable, and none utilize a validated cultural measurement instrument. This study introduces the Culturally Contextualized Digital Transformation Model (CC-DTM), a four-layer theoretical architecture that integrates the TOE framework, TAM constructs, and Hofstede’s cultural dimensions, operationalized as individual-level espoused values rather than national aggregate scores. The model incorporates a novel meso-level construct, Ecosystem Density, which mediates the relationship between environmental context and organizational readiness. The CC-DTM specifies 22 constructs and 15 directional hypotheses, organized into an initial empirical agenda (H1–H12) and deferred extensions (H13–H15). Additionally, a three-configuration typology based on internal SME attributes is developed. A two-phase validation roadmap, consisting of expert-panel content assessment and configurational case illustration across ten Chilean SMEs, is proposed.