Although undergraduates from all class backgrounds work while attending college, little is known about how students approach finding work and the benefits they reap from different on-campus roles. Drawing on interviews with 110 undergraduates at Harvard University, we show that in the absence of clear institutional expectations surrounding on-campus work opportunities, students draw on class-based strategies to determine which jobs are "right for them." Upper-income students pursued "life of the mind" jobs that permitted them access to institutional resources and networks. Alternatively, lower-income students pursued more transactional "work for pay" positions that yielded fewer institutional benefits and connections. The consequences of these differential strategies were amplified during COVID-19 campus closures as work-for-pay positions were eliminated while life of the mind continued remotely. Through documenting heterogeneity in work experiences, we reveal a class-segregated labor market on campus and extend previous analyses of how university practices exacerbate class differences and reproduce inequality.