This study sought to ascertain the discontinuities of the virtual environment for Ghanaian firms, determined the critical success factors of implementing telecommuting and examined the effect of telecommuting on organizational performance. A quantitative research approach was adopted. Data was collected from knowledge workers (N=310) in Higher Education Institutions, Accounting and Audit firms, Banking and Insurance firms as well as Telecom and IT firms. A PLS-SEM analysis was carried out to explore the structural relationships among the research variables. The study relied on the socio-technical systems theory to test how multiple social and technical factors co-jointly influence organizational performance. The findings show that intra-organizational communication, learning and knowledge sharing (LKS), employee characteristics (social factors) and technology and media richness (technical factor) are critical success factors (CSFs) for telecommuting. These factors were found to have differential impacts on organizational performance at the individual, team or managerial levels.