Life course criminology has long argued that having a job may act as a turning point in trajectories of offending, moving individuals toward conventional activities. However, while finding and keeping a job are considered one of the key challenges inmates face as they move back into society, there is limited research on the dynamics and trajectories of post-prison employment. Little is also know about whether work characteristics and its relation to crime affect employment trajectories following release. Using data from the study ``Reintegration, desistance and recidivism among female inmates in Chile'' (RDFC), our paper describes trajectories of employment among a cohort of 225 women released from prison in Santiago, Chile and followed during the first year after release. We use sequence analysis to explore monthly patterns of employment considering different types of work (i.e., self-employed / employed, legitimate / under-the-table). To better account for the complex relationship between work and crime, we include offending as another type of income-generating activity. Finally, we use cluster analysis and regression models to explore which individual characteristics are associated with employment and offending trajectories. Our results show a significant level of heterogeneity in employment trajectories by job type, and the importance of considering work and offending to obtain a more complete picture of the dynamics of employment during reentry.