Small enterprises are beginning to utilize Geographic Information Systems (GISs) and spatial technologies. Since these technologies have only recently become widely available for small enterprises, there are challenges including costs, training, skilled workforce, data gathering and management, and competitive strategy. Two conceptual theories of GIS strategy are discussed with respect to small enterprises. The goal of the present exploratory paper is to analyze readiness for undertaking spatial technologies, with a focus on GIS strategy and competitiveness. The research questions are analyzed through in-depth case study analysis of two small enterprises in southern California and results are interpreted based on the conceptual theories. The findings show that alignment theory is useful in assessing the potential for GIS. The evolutionary framework for strategic GIS is supported in two of the theory’s three dimensions. The paper offers recommendations on differences for small enterprises, versus medium and large ones in readiness and GIS strategy.