We propose a brick-and-click prioritization tool that aids retailers in the transition from a multi-channel to an omni-channel strategy. The developed tool represents a strategic roadmap that goes beyond the limitations of existing literature, which either observed the transition towards omni-channel strategy theoretically or provided static, diagnostic, qualitative multiple channel classification frameworks. Quantitative measurability, benchmark potential, and predictive capacity of a multiple channel prioritization tool are introduced by applying the multiple criteria decision aiding method, dominance-based rough set approach. The output of the method is a set of “if-then” decision rules. Prescriptive in their nature, they guide managerial focus on channel aspects relevant to implementing a specific multiple channel strategy. We propose a novel attribute significance index that measures the importance of each KPI in reaching a specific multiple channel strategy. This allowed us to derive possible multiple channel pathways and optimize the retailer’s multiple channel transition strategy. The findings identified the importance of optimizing online channel sales concentration and focus, two attributes proposed by the authors to better depict the channel goal dimension in the multiple channel environment, as key preconditions for implementing the omni-channel strategy.