Background: Our research delved into exploring various selected facets of AI-driven employee engagement, from the gender perspective, among Slovenian entrepreneurs. Methods: This research is based on a random sample of 326 large enterprises and SMEs in Slovenia, with an entrepreneur completing a questionnaire in each enterprise. Results: Findings suggest that there are no significant differences between male and female entrepreneurs in Slovenia regarding various aspects of AI-supported entrepreneurial management practice including the following: AI-supported entrepreneurial culture, AI-enhanced leadership, adopting AI to reduce employee workload, and incorporating AI tools into work processes. The widespread integration of AI into entrepreneurship marks a transition to a business landscape that values inclusivity and equity, measuring success through creativity, strategic technology deployment, and leadership qualities, rather than relying on gender-based advantages or limitations. Our research also focused on the identification of gender differences in path coefficients regarding the impact of the four previously mentioned aspects of AI on employee engagement. While both genders see the value in using AI to alleviate employee workload, the path coefficients indicate that female entrepreneurs report higher effectiveness in this area, suggesting differences in the implementation of AI-integrated strategies or tool selection. Male entrepreneurs, on the other hand, appear to integrate AI tools into their work processes more extensively, particularly in areas requiring predictive analytics and project scheduling. This suggests a more technical application of AI in their enterprises. Conclusions: These findings contribute to understanding gender-specific approaches to AI in enterprises and their subsequent effects on employee engagement.