Abstract: Internet software as a service (SaaS) platform and methodology for generating targeted bond recommendations to institutional fixed income investors that are customized to each buying institution's unique investment strategy, and provides selling institutions with demand information on each cusip they need to sell. The methodology incorporates sophisticated machine learning algorithms, decision trees, and clustering techniques from data science that quantify similarity between bonds. The system can then effectively utilize the calculated bond similarity to make targeted bond and market color recommendations, optimize bond search tools, and provide much needed intelligence into the antiquated search tools currently used in bond markets. The system will reduce or eliminate tedious and time consuming search tasks for bond buyers, and provide bond sellers with valuable pre-trade information, transparency, and a means of connecting with the highest demand in the market on positions they need to sell.