Informed by social information processing (SIP) theory, in this study, we assessed the associations among family supportive supervisor behaviors (FSSBs) as perceived by subordinates, subordinate work engagement, and supervisor-rated work performance. Moreover, we explored the role of family supportive organizational culture as a contextual variable influencing our proposed associations. Our findings using matched supervisor–subordinate data collected from a financial credit company in Mexico (654 subordinates; 134 supervisors) showed that FSSBs influenced work performance through subordinate work engagement. Moreover, the positive association between subordinates’ perceptions of FSSBs and work engagement was moderated by family supportive organizational culture. Our results contribute to emerging theories on flexible work arrangements, particularly on family supportive work policies. Moreover, our findings carry practical implications for improving employee work engagement and work performance.