Although Sears officials have touted its Shop Your Way loyalty program as the key lever in the venerable company’s return to significant brand loyalty, something has gotten in the way of their strategy: A highly challenging retail environment. Given its mantra of being an “an asset-light, member-centric integrated retailer,” with the loyalty program as its focal strategic point, the fiscal second quarter was not kind to Sears as it logged a net loss of $395 million while same-store sales at Kmart and Sears fell 3.3% and....

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