As small- to medium-sized enterprises struggle with IT management, an increasing number appoint Fractional CIOs, i.e., CIOs that work part-time for multiple organizations simultaneously. We use Q-methodology to empirically evaluate the relative importance of factors for Fractional CIO engagement success and find that trust, top management team support, and the Fractional CIO’s integrity are most important. Further, we identify three groups of Fractional CIOs: Strategic IT Advisors, Full-ownership CIOs, and Change Agents. Our results guide organizations when hiring and working with Fractional CIOs and provide the basis for further research on Fractional CIO archetypes.