Although higher education has been long heralded as a powerful engine for making upward mobility, the upwardly mobile are still significantly underrepresented and achieve lower levels of success in elite professions. To better understand how the class gap in career attainment and success persists among the highly educated, this dissertation examines class differences in the type of careers individuals esteem and pursue; and their within-organizational experiences in establishing careers beyond the school and recruitment settings. Chapter 1 draws on an 18-month case study of junior attorneys at an elite law firm to examine variations in their early career establishment processes. I first articulate how a fluid organizational structure creates a dilemma for junior attorneys when managing work requests from many partners. Interestingly, their approaches to this dilemma are closely related to their social background, with most first-generation college graduates taking less effective approaches – they are more likely to either say yes to all and get overwhelmed or struggle to source work in the first place. Chapters 2 and 3 use unique survey data from Ivy League undergraduates to explore students’ diverse perspectives of what careers they deem desirable and prestigious. Chapter 2 finds that students from more affluent backgrounds are likelier to want to pursue elite professions than their lower-income peers, even after accounting for various class advantage mechanisms. Over half the difference is explained by higher-income students’ higher inclinations for enterprising careers and lower preferences for artistic and prosocial careers. Chapter 3 finds contrasting roles of class and race in shaping students’ job status beliefs. Whereas students from privileged class origins show stronger allegiance to the conventional sense of career prestige hierarchy, white students diverge more significantly from it. Together, Chapters 2 and 3 show the potential supply-side mechanisms of class differences in representations in elite professions. By elucidating novel mechanisms underlying the reproduction of class gaps in elite professions, this dissertation contributes to the literature on class, careers, workplace inequality, and social stratification.