Computing and information sciences (CIS) careers in the United States are expected to grow faster than the average occupation between 2019 and 2029 and educational requirements for these positions span subbaccalaureate and baccalaureate degrees. Despite secondary curricular interventions, the population of people who pursue CIS pathways are not diverse by race, ethnicity, socioeconomic status, or gender. This study applies situated expectancy-value theory to investigate the motivational factors which influence the decision to pursue postsecondary CIS degree programs for students in the High School Longitudinal Study of 2009 (n = 18,730). Prior CIS experiences are associated with increased odds of declaring subbaccalaureate and baccalaureate CIS within three years of high school, but several math-related factors are associated only with pursuing baccalaureate CIS. These results have implications for designing interventions that encourage more students to pursue computing careers and understanding why students choose between two postsecondary educational paths.