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Despite the fact that Saudi Arabia is a leading producer of oil and natural gas, a member of G-20, has the largest and fastest growth of ICT marketplaces in the Arab region, and is very wealthy, online retailing activities are not progressing at the same speed as its growing ICT marketplace. For this reason, the attitudes of retailers in companies at different stages of e-commerce maturity were investigated to determine what factors are causing this problem. The data collection included two stages: first, interviews with 16 retailers and, then, based on the outcomes of the interviews, a quantitative study designed to test and further explore the qualitative interview findings with a sample of 153 retailers in companies at different stages of e-commerce maturity. The results showed striking differences between retailers as a function of the stage of growth of their companies in regard to factors relating to their perceptions of consumers and to organizational factors. At the same time, the results showed agreement between retailers in companies at different stages in relation to environmental factors. The investigation helped to identify the incentives and barriers for each stage of maturity and makes recommendations of what could be done to help companies move from one stage to the next.