In information systems and organization theory research, the alignment or fit between information technology (IT) and organizational structure has long been hypothesised to be a sine qua non for success. However, few solid results have been found linking this relationship to enterprise level performance, as problems abound in defining and measuring IT, performance and the fit between technology and structure. In view of this, an empirical study was conducted among 108 small and medium-sized manufacturing firms, using a comprehensive instrument to measure overall IT sophistication along two dimensions, namely IT usage and IT management. Taking organizational size and environmental uncertainty into account, it was found that IT sophistication is positively related to structural sophistication, IT usage is positively related to organizational performance, and the relationship between IT management and structural sophistication is stronger among the better-performing firms than among the worst-performing firms.