U.S. service members transitioning from the military face formidable challenges to securing meaningful employment matching their preferences and qualifications. Despite diverse employment services, many veterans settle for dead-end jobs. This study examined personal characteristics predicting successful employment outcomes. In a secondary analysis of a controlled trial assessing 2-year employment outcomes for 205 transitioning veterans with service-connected disabilities participating in a career coaching program, multivariate regression analyses were conducted to identify personal characteristics associated with employment outcomes, including characteristics differentiating who benefits more from a career coaching program, compared to usual services. Two employment outcomes were examined: job acquisition and employment earnings. The single best predictor of job acquisition was assignment to the career coaching intervention. Among 18 demographic, military service, and health and well-being measures, the only predictor of job acquisition was gender (91% of men and 79% of women worked during follow-up). Twelve personal characteristics were associated with mean monthly earnings from employment, including four demographic measures, three military service measures, and five measures of health and well-being. Disability ratings did not predict employment outcomes. Overall, career coaching helped veterans gain employment, regardless of their personal characteristics. Three personal characteristics differentiated veterans who benefited more from career coaching. Veterans reporting alcohol use and those who had a longer period of military service benefited more, as did veterans who were not depressed. The authors conclude that most veterans obtain civilian employment soon after separation from the military, but personal characteristics strongly influence their employment earnings.