The Customer Relationship Management (CRM) practice involves reengineering of various customer-related processes. The objective of this study is to understand how CRM system enables the business to transform its processes especially the selling chain into the customer-centric ones. This study identifies opportunities and barriers to the selling chain reengineering in the Korean Insurance Industry. The Korean insurance company has a unique structure composed of traveling sales people. Much of the sales are done through visiting potential customers based on personal relationships. The Korean insurance industry is facing deregulation in 2004. The uniqueness in organizational characteristics and sale culture as well as industry future presents unique challenges and opportunities of the selling chain reengineering. This study uses multiple case studies.