Purpose This study empirically tests whether and through which mechanisms digital strategy (DS) influences digital organisational culture (DOC) in small and medium enterprises (SMEs). While prior research often treats DOC as a precondition for digital transformation, our study reverses this direction by conceptualising DS as a driver of cultural change. Design/methodology/approach Grounded in contingency and strategic choice theories, the study develops and tests a parallel mediation model linking DS to DOC through two mediators: digital transformational leadership (DTL) and digital capabilities (DCs). The model is evaluated using cross-sectional survey data collected from 160 SMEs operating in Poland's energy sector – a highly regulated and technologically evolving environment. Findings The results confirm that DS significantly shapes DOC, both directly and indirectly. DCs and DTL act as parallel mediators, with DCs emerging as the stronger pathway. DS remains the most influential predictor, underscoring its strategic role in driving cultural alignment. Research limitations/implications This study employs a cross-sectional, single-respondent design and focuses on SMEs in one highly regulated national sector, which may constrain causal inference and generalisability. Future studies should adopt longitudinal or multi-level approaches and extend inquiry to larger firms or alternative institutional environments. Although DCs and DTL are key mediators, variables such as agility, collaboration or innovation climate may further influence DOC. These findings provide a theoretical basis for investigating how strategy-driven change unfolds in constrained contexts and highlight avenues for refining strategic-cultural alignment models. Practical implications To foster digital organisational culture and accelerate transformation, SME leaders should prioritise strategic digital alignment and invest in leadership development and capability-building. The inherent agility and flat hierarchies of SMEs enhance their responsiveness to cultural change when strategically guided. Policymakers can amplify this potential by offering targeted, sector-specific incentives, particularly in regulated industries – to lower adoption barriers, reduce compliance burdens and catalyse sustained digital-cultural convergence. Originality/value This paper contributes to digital transformation literature by reframing the DS–DOC relationship through a contingency-theoretic lens. It clarifies the mediating roles of capabilities and leadership in shaping DOC and empirically tests this model in an under-digitised and heavily regulated sector. By focusing on Polish energy SMEs, the study addresses a significant contextual gap in the literature.