Drawing from a total rewards perspective, we introduce three work outcomes (namely, extrinsic, social, and intrinsic) as determinants of person–organization (PO) and person–job (PJ) fit perceptions of new IT employees. Gender is proposed as a moderator of the relationships between valuations of different work outcomes and fit perceptions. We found support for our model in three separate studies. In each of the studies, we gathered data about the work outcomes and fit perceptions of IT workers. The studies were designed to complement each other in terms of cross-temporal validity (studies were conducted at difference points in time over 10 years, in periods of differing economic stability), and in terms of prior work experience (entry-level workers in studies 1 and 2, and those with prior work experience starting new jobs in study 3). All three studies also included data both pre- and post-organizational entry in order to further validate the robustness of the model. The studies largely supported our hypotheses that (1) the effect of extrinsic outcomes on PO fit was moderated by gender, such that it was more important to men in determining their PO fit perceptions; (2) the effects of social outcomes on both PO fit and PJ fit was moderated by gender, such that it was more important to women in determining their fit perceptions; and (3) intrinsic outcomes influenced perceptions of PJ fit for both men and women. We discuss implications for research and practice.