Background: Many programs emphasize subsequent pregnancy prevention and high school graduation among teenage mothers; however, less is known about their ability to increase financial earnings from employment opportunities while concurrently enrolled in school. This study evaluates factors influencing employment status among teenage mothers after enrolling in a community-based randomized intervention. Methods: Project Mothers and Schools (PMAS) initiative participants were surveyed at baseline and 12 months after enrollment. The 56 control group participants received homebound education and family case management, whereas the 59 intervention group participants received these basic-level services as well as group parenting time, life skills, and leadership training. A generalized estimating equation was used to identify statistically significant changes associated with the intervention. Results: Participants were significantly more likely to receive money from their jobs at postintervention relative to baseline (OR = 4.75, p = 0.023); however, this change was not statistically significant when comparing the control group to the intervention group. At postintervention, those who received money from parents were significantly less likely to receive money from their job (OR = 0.12, p = 0.002). Conclusions: While PMAS benefited participants in terms of employment, the role of parental support requires additional investigation to determine its influence on teenage mothers' ability to achieve financial independence.