The online retailing industry activity has been steadily increasing in the past couple of years, due to the wide product offerings and provides customer convenience. The Philippines is part of the Asian population with steadily increasing online retailing activity, making the country one of the fastest-growing e-commerce markets in Asia. With the increased number of online retailers, different factors can now be determined, as well as an implementation framework for brick-and-mortar retailers' consideration to expand into online retailing. A survey was conducted to measure the perception of Philippine-based brick-and-mortar retailers with regard to key factors to expand into online retailing. The research study used the Technology Acceptance Model (TAM) framework and Structural Equation Modeling (SEM) in determining the significant factors that retailers consider in their expansion into online retailing. Cybersecurity, IT Infrastructure, Capital Cost, Reach, and Online Retailing Industry Attractiveness were all found to have a significant effect on Retailer's Decision to Expand into Online Retailing. A readiness index was formulated from the results of the SEM, which in turn aided in developing an implementation framework catered to different levels of readiness.