Growing segments of the Kenyan population are demanding higher education. Recent statistics indicate an increase in university enrolments as well as rapid expansion in higher education to meet the rising demand. Many Kenyan parents are investing significant resources and enduring major sacrifices to ensure their children obtain a university education. Similarly, the Kenyan government is also undertaking several measures to ensure that university education is available and accessible to a wide spectrum of Kenyans. However, the high rate of youth unemployment facing the country poses a great threat to the successful transition of university graduates into the workforce. Trends indicate that unemployment among recent university graduates is on the rise, which in turn is negatively impacting returns on higher education investments. This study sought to understand the transition experience of baccalaureate graduates in Kenya so as to inform the discourse on school-to-work transitions in Kenya. Using the concurrent nested mixed methods strategy; a predominantly quantitative electronic survey was administered to 2010, 2011 and 2012 alumni of a private university in Kenya. The objective of the study was to understand how graduates transitioned into their post-graduate occupations; to identify the strategies they employed to facilitate the transition; and to identify the factors that facilitated or impeded their desired transition outcome. One hundred and fifty three (153) alumni responded to the survey. Findings show that graduates transitioned into their desired post-graduation plans, which mainly included joining the workforce or pursuing further academic studies. Also, majority of graduates preferred careers as employees in the private and not-for-profit sectors, although there were some significant differences in the transitional experiences by gender. Graduates mainly depended on immediate family and friends as key resources to facilitate their transition. Lastly, graduates had difficulty adapting and keeping up with the new adult roles and responsibilities.