Within established organizations, employee innovative behavior is vital for the long-term survival of firms. Employee individual entrepreneurial orientation (IEO) represents tendencies by an individual toward innovativeness, proactiveness, and risk-taking behaviors. IEO is an emerging construct in the entrepreneurship domain, and while an important construct, contextual factors can influence the employee’s demonstration of innovative work behavior (IWB). The degree of IEO similarity or fit between an employee and their supervisor is theorized to amplify the employee’s innovative work behavior. To guide this research, person-supervisor fit (P-S fit) theory and strategic consensus theory provided a theoretical framework to investigate the relationships between these constructs. Drawing on a sample of employees across all levels of an established firm, two sets of data were analyzed: perceptions of supervisor IEO fit (n = 265) and matched pairs of IEO between employee-supervisor dyads (n = 132). The results suggest that employees’ levels of innovativeness and proactiveness are positively associated with IWB. Additionally, the data provided partial support for the moderation effect of supervisor IEO proactiveness fit and supervisor IEO risk-taking fit on amplifying employee IWB. The results suggest that the level of supervisor IEO fit for the proactiveness and risk-taking dimensions of IEO magnify the IEO-IWB relationship when employees have low levels of proactiveness tendencies and low levels of risk-taking tendencies. This research offers theoretical and practical implications by examining IEO, within the context of supervisor fit, in promoting employee innovative behaviors within the workplace.Keywords: individual entrepreneurial orientation, innovative work behaviors, person-supervisor fit, strategic consensus, innovativeness, proactiveness, risk-taking