IT organizations use strategic IT benchmarking (SITBM) to improve business-IT alignment or for developing or revising IT strategies. However, despite SITBM’s long tradition, many initiatives don’t result in the desired improvements, or fail completely. Because the extant literature on general benchmarking and strategic IT management does not contribute to overcoming these challenges, we apply a deductive-inductive research design to better understand which factors distinguish successful and unsuccessful SITBM. Analysis of three IT organizations that have conducted SITBM reveals that traditional project-level perspectives of benchmarking are insufficient to explain its success. We argue that project level factors - high-quality methodologies, management support, and integration of benchmarking into IT’s strategic planning process - are necessary but not sufficient conditions for SITBM success. Rather, these project-level facets trigger important effects on the individual level. We show that the individual level is instrumental for explaining SITBM success, especially by ensuring the buy-in of relevant project team members involved based on their acceptance of the results and procedures – a perspective not yet discussed by benchmarking research.