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This teaching case discusses the challenges facing Sears, Reobeck and Co, a leading retailer in United States, in its efforts to transform itself into an effective brick-and-click organization. In face of intense competition from other retailers and online e-Tailers, Sears has continually expanded its online efforts in e-Business transformation. This case traces the key e-Business initiatives taken by Sears and highlights significant managerial challenges that were encountered during the formulation and execution of an effective e-Business transformation strategy. The case presents the issues faced by a new CIO who had taken over the technology and e-Business affairs at Sears at the end of 2002.