In today’s digitally connected environment retailers need to interact with customers on multiple channels and touch points simultaneously (or even interchangeably) to deliver seamless shopping experience. The customer expectations have also seen gamut of changes; they are agnostic to the lines dividing various channels and expect convenient delivery options like click & collect, drop shipment and delivery lockers. In this context, the retailer’s supply chain should have the agility and efficiency to provide convenient delivery options while striving to deliver faster with improved precision. In this paper we have discussed a series of challenges that a retailer will face in evolving to a flexible supply chain that supports multi-channel delivery options. We’ve also recommended important considerations for retailers to be successful & mature in customer delivery promising and fulfillment.