Purpose – This study examines the determinants of an effective digitalization strategy in entrepreneurial lifestyle and high-growth firms. It explores the role of entrepreneurial orientation (EO) dimensions alongside technology readiness and Fourth Industrial Revolution (4IR) knowledge in driving digital transformation. Design/methodology/approach – The study employs a fuzzy set qualitative comparative analysis (fsQCA) approach to identify the configurations of EO and technology readiness that led to high digitalization strategy adoption. Data were collected from 208 German SMEs through a structured survey, measuring digitalization strategy maturity, EO dimensions, 4IR knowledge and technology readiness. Findings – Results reveal multiple pathways to achieving an effective digitalization strategy. Both lifestyle and high-growth firms benefit from strong EO components, with risk-taking and proactiveness being critical factors. However, technology readiness plays a significant role in digital transformation success. Interestingly, 4IR knowledge is not a primary determinant but acts as a complementary factor. Originality/value – This study contributes to the digitalization and entrepreneurial research domains by demonstrating that different EO configurations in combination with 4IR knowledge and digital readiness drive digital transformation. © 2025 Natanya Meyer, Chris Schachtebeck, Cheng-Feng Cheng, Christoph Stöckmann and Tobias Gössling
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