Despite the satisfactory progression of women in the workforce over the years, recognition of women in the upper echelons of the finance sector is still falling behind. This study examines the impediments that hinder women's representation in the boardrooms in Sri Lankan private sector finance organizations using Ragins and Sundstrom's (1989) four levels of analysis as the theoretical lens. We employed thematic analysis to explain how the individual, interpersonal, organizational, and social level factors affect the participation and progression of the female workforce. Perceived glass ceiling, individual role choices, the inadequacy of role models and mentoring, lack of networking opportunities, gendered organizational structures and socio-cultural norms were identified as pivotal factors affecting the glass ceiling. Understanding the interrelationship between these factors helps us to better understand the phenomenon of female leadership in organizations.