This article presents the development and validation of DigSME, a tailored Digital Maturity Model designed to support the digital transformation of small and medium-sized enterprises (SMEs) in Ukraine. The scientific novelty lies in the creation of a customizable, context-sensitive self-assessment tool that addresses the digital inequality faced by SMEs in transitional and post-conflict economies. Unlike existing models developed for mature markets, DigSME integrates strategic, technological, and human resource indicators that reflect the unique socio-economic conditions and institutional constraints of Ukrainian SMEs. The article provides a comprehensive analysis of 13 global digital maturity models and highlights their structural limitations when applied to the Ukrainian context. Based on this analysis and stakeholder consultations from EU-funded and UK-funded research initiatives, a new three-block architecture − Scope, Technologies, and Integration − was designed. The DigSME model includes 13 indicators and 52 sub-indicators, offering a nuanced diagnosis of SMEs’ digital capabilities. An online platform was developed for testing the model, enabling SMEs from Ukraine and the UK to conduct a self-assessment and receive personalized recommendations and strategic roadmaps. The model computes a Digital Maturity Index (DMI) based on weighted technical and organizational scores. Visualization tools, benchmarking capabilities, and downloadable guidance documents enhance its practical applicability. The results of pilot testing confirmed the model’s usability and relevance. Moreover, the platform allows for clustering SMEs by maturity levels and regional contexts, facilitating data-driven policymaking. The study concludes that DigSME serves as both a diagnostic and developmental tool, supporting more equitable digital integration of SMEs into the global economy and informing future digitalization policies.