Digital transformation has become an inevitable choice for firm development， and top executives， as core decision-makers， play a crucial role in this process. Based on the upper echelon theory and real option theory， it used Shanghai and Shenzhen A-share listed manufacturing firms from 2007 to 2023 to examine the effects of executives’ digital background and managerial myopia on enterprise digital transformation， as well as the moderating roles of firms’ risk perception and regional speculative culture. The results show that executives’ digital background significantly promotes digital transformation， whereas managerial myopia exerts an inverted U-shaped effect on enterprise digital transformation. When enterprises perceive higher risks or are located in regions with a stronger speculative culture， the positive effect of executives’ digital background becomes stronger， while the inverted U-shaped relationship between myopia and digital transformation becomes weaker. Heterogeneity analysis shows that for non-state-owned enterprises and highly competitive manufacturing enterprises， executives’ digital backgrounds significantly promote enterprise digital transformation； for state-owned enterprises and highly competitive manufacturing enterprises， there is a significant inverted U-shaped relationship between executive myopia and digital transformation. By integrating executive capability and cognitive preference， it extends the theoretical explanation of the micro-level antecedents of enterprise digital transformation and shows that the effects of executive characteristics are not simply linear， but significantly context-dependent. The findings also provide practical implications for cultivating digitally capable executives， optimizing executive team structure， and improving mechanisms for digital talent development and allocation under different uncertainty conditions.