Background and Purpose In 2010, 20.5 million were students enrolled in bachelor's degree programs in four-year public universities in the United States 1. Approximately, 60% of these were first-generation students (students whose parents did not earn a four year college degree)2. However, what has been largely overlooked in research on first-generation students in the United States is the issue of post-degree employability or the transferability of education into graduate level employment opportunities. The primary purpose of this research, therefore, was to explore if and how the educational biography of first-generation students impacted their transition into graduate level positions in the corporate sector. Research Methodology The study was guided by three research questions: how first-generation graduates described the process of navigation into the corporate world; how they perceived their transition into graduate level employment; and what role they envisaged for educational institutions in supporting this transition. The researcher conducted a qualitative inquiry of the transition experiences of 14 first-generation graduates employed in the financial industry in a metropolitan city in the United States and collected data through semi-structured interviews. Using a phenomenological approach, the researcher described and interpreted the thoughts, feelings, and experiences of these 14 individuals with regard to their transition from education to employment. Findings This study indicated that the education level of parents seemed to be a more serious determinant and driver of the immediate occupational outcomes of first-generation students, more so than their racial, social or economic background. The study found that restricted access to cultural and social capital within the families resulted in first-generation graduates being disadvantaged on four grounds: ineffective career decision making skills; lack of familiarity with corporate culture and expectations; inadequate preparation for the world of work; and lack of access to professional networks. Conclusions The four disadvantages resulted in first-generation graduates starting at entry level positions in the corporate sector, having to invest time and effort to learn corporate culture and expectations, experiencing delayed growth within the organization, along with facing a possibility of being discriminated against during recruitment process. This study clearly indicated the need for policy and programs that could support transition of first-generation graduates into graduate level employment. The study also found the need for faculty to play a proactive role in enhancing the career orientation of first-generation students, the importance of lobbying for more inclusive recruitment practices in the corporate sector, and the significance of creating graduate level positions to match the increasing supply of graduates. 1U. S. Census Bureau (2012). The 2012 statistical abstract: The national data book. 2. U.S. Department of Education, NCES (2010, September). Web tables: Profile of undergraduate Students 2007-2008.