This study explores the unique dynamics of women's entrepreneurial leadership within Stewart's role demands-constraint-choice framework in Greece. Addressing the underrepresentation of women entrepreneurs in Greek literature, this study identifies distinct motivations and leadership styles through qualitative analysis of semi-structured interviews with Greek women entrepreneurs. The findings reveal a complex array of motivations that diverge significantly from those prevalent in more developed economies driven by personal, sociocultural, and economic factors. Key motivations include financial independence, family support, societal betterment, and personal fulfillment. This research not only enriches the discourse on international entrepreneurship and women's studies but also provides a deeper understanding of Greek women entrepreneurs’ motivations and leadership decisions within their socio-economic and cultural contexts. The practical implications drawn from the study offer strategic insights for policymakers, educators, and industry professionals to cultivate an environment that nurtures women's entrepreneurial leadership in Greece and other similar economies. This enhances theoretical and practical knowledge in international entrepreneurship and gender studies, contributing to a broader understanding of women's entrepreneurship's economic and social impact.