As information technology (IT) continues to be an integral yet evolving component in work settings, organizations need to ensure that they realize value from IT. Prior studies that examined the post-adoption consequences of IT use in terms of employee job outcomes were inconclusive with respect to the magnitude and direction of these impacts—i.e., positive, negative, and nonsignificant impacts of IT use on job outcomes. The question of under what conditions IT use leads to favorable job outcomes over time thus remains largely unanswered. We develop a model of IT-related contingencies that integrates core constructs from the IT adoption research with two key job outcomes: job satisfaction and job performance. We hypothesize that, in the post-adoption phase, technology-job fit will be a key moderator of the relationships between IT use for supporting sales operations and job outcomes. Further, we suggest a theoretical extension of the classical predictors of IT adoption, perceived usefulness and perceived ease of use, as we expect them to moderate the effect of IT use on job performance over time. We tested our model in a longitudinal field study among 295 field sales personnel over a 24-month period. We found that, although IT use had a negative effect on job satisfaction during the post-adoption phase, this effect was moderated by technology-job fit such that the negative effect was significantly attenuated by technology-job fit. We also found that perceived usefulness, perceived ease of use, and technology-job fit enhanced the positive effect of IT use on job performance. Our findings offer insights on the mechanisms and conditions related to the post-adoption impacts of IT use on key job outcomes.