The IT-business strategic alignment (ITBSA) aims to promote greater IT effectiveness by making it active in the firms’ competitiveness agenda. Despite the relevance of the theme, ITBSA is not free from criticism. Ciborra criticized how ITBSA research programs have been developed and its sufficiency for an effective strategic planning. This article shows how a business model in a small real estate firm was deployed for revenue generation through an Action-Research (AR) conducted to evaluate Ciborras’ criticism. The results show ITBSA critics from the field and a new business model direction. The ITBSA was concluded to have structured the strategic discussion; however, Ciborra’s inputs about the importance of bricolage, cyclical learning was conquered by an influence of the researcher as an agent of change applying AR under the critical theory paradigm. We suggest future research with more comprehensive literature review about our usual assumptions of economic rationality.