As a developing country, Bangladesh is still less advanced in using the latest technologies such as websites, e-commerce, high-speed internet, point of sales (POS), etc. which is a great barrier in SME development. Proper implementation of technologies can achieve the full potential of this valuable sector. This paper aims to find out the feasibility factors of the implementation of a web-based point of sales system for SMEs in Bangladesh. The implementation of such kinds of systems will help SME entrepreneurs to achieve more potential from their businesses. A comparison of ICT developments, technologies, and POS system adaptation scenarios between Indonesia and Bangladesh is presented based on secondary data sources. The study indicates the current challenges to implement new technologies in SME sectors. The research found out the recent technological development conditions in Bangladesh. The results indicated that the implementation of a web-based POS system is feasible for SMEs in Bangladesh if the challenges can be successfully overcome. The authors suggest priority steps be taken by the government and private agencies for POS system adaptation by the SMEs in Bangladesh.