As the use of contracting for Information Technology (IT) services steadily increases, IT managers are challenged with reconciling the need for flexibility achieved through the use of contract workers, with the need to understand the factors that maximize the performance and behaviors of contract and permanent IT workers. While several research studies have focused on motivation factors, they have focused either on environment factors such as jobs, or individual factors such as the need for challenge, versus focusing on both environment and individual factors as joint determinants. Also, studies that have examined motivation factors of contract workers, lack a comparison to permanent workers. To bridge these gaps, this dissertation develops a model that compares not only the job characteristics experienced (environment factor) by contract and permanent IT workers, but also the job characteristics expected and preferred (individual factors) by contract and permanent IT workers. Further, it applies a complementary needs-supplies perspective of Person-Job Fit Theory to predict the effect of the expected-experienced job characteristics fit and the preferred-experienced job characteristics fit on the performance and behaviors of contract and permanent IT workers. A partial least squares structural equation modeling (PLSSEM) approach is utilized to test the effect of fit. The study sheds new light on Person-Job Fit and its ability to affect the performance and behaviors of contract and permanent IT workers, while avoiding the methodological limitations of prior studies in this area.