Managers are heavily engaged in strategic decision-making for businesses, particularly in a changing environment. One of the most important decisions for online small businesses, as part of their strategic planning, is selecting relevant features on their websites, both to attract and interact with consumers. However, only a few Australian small businesses use strategic tools for selecting their website features. As a result, businesses lose potential domestic sales in the business-to-consumer (B2C) sector. The aim of this study is to determine the relationship between factors that influence consumers’ online purchasing, and owner/manager strategic decisions in selecting relevant features for websites. Results from employing qualitative case studies with small business owner/managers, and a content analysis of website features, inform the design of a Decision Support Systems (DSS) framework. This may assist owner/managers’ strategic decisions to implement competitive features on B2C websites that ultimately attract more consumers.