The purpose of this study was to understand the lived experiences of Jamaican Expatriate Female C-suite executives in the diaspora of working in Multi-national Companies (MNCs). A further question to be answered was the meaning they derived from their experiences. With little research emerging from the Caribbean about this elite class of professionals, the research intended to expose the challenges faced as an outsider in unfamiliar spaces. Research on other groups have exposed limiting factors to women’s progress in MNCs. Critical Race Theory with a brief mention of Critical Human Geography and Intersectionality are lens applied to critique the experiences of the eight participants. This research mined the extant literature that looked at navigating barriers, disrupting stereotypes and gender diversity in international careers. The method of inquiry applied to this research was existential phenomenology and its utility in getting to the essence of the women’s lived experiences highlighted the glass-border phenomenon. In reflecting on the outcome, this research opens the door for scholars and practitioners alike, to critically assess the expatriate literature and to probe further the complex relationship between international business, the movement of black talent across geographic and culturally diverse boundaries and the challenges encountered. The results of this study illuminated several themes from the participants textural descriptions: (1) Moving from Invisible to Visible—Disrupting Bias; (2) Who am I?—Identity, Gender and Heritage; (3) Renegotiating the Rules of Engagement paired with Re-branding the Role and Authority of Women in Business; (4) Male Sponsorship Leads to Acceptance; (5) Improving Skill and Competency Capital for New Roles; (6) Building and Maintaining Bridges—Network Management.