The most recognized application of Geographic Information Systems (GIS) for retailers is to assist with the site selection process. For an expanding retailer, GIS can help optimally deploy multiple stores across space. In a Darwinistic sense, every retailer will eventually reach a point of real estate maturity when it can no longer deploy new stores without significantly cannibalizing its existing stores. Retailers can no longer grow their revenues simply by opening new stores; they must evolve their business strategies. Along those lines, a theory of retail chain expansion and maturity is presented whereby retailers expand in waves with alternating periods of faster and slower growth. Once a retailer reaches a mature stage, the business can experience challenges. Empirical evidence is provided for Target and Walmart. It is at this stage when the bevy of powerful GIS tools can be utilized to continue to grow the business. The story of West Marine is presented as it transitions from a marine supply retailer to a waterlife outfitter. It adopted GIS as its location intelligence platform to help make better decisions to maximize profitability across markets. GIS aids in ensuring that the store locations are not only optimally deployed, but that they are the proper size and format and have the appropriate merchandise given the type of real estate and trade area characteristics.