Abstract: The present invention represents a web-based, CRM-integrated system and method for unlocking the creativity of salespeople at all levels when selling to different buyer personas within a buying community throughout the buying cycle. The system of the present invention may be flexible and may integrate the collection of data through questions posed to a user, as well as secondary data sources. This data may be utilized to create a tool for the sales process and to facilitate learning by salespeople. The tools created and utilized by the system may include personas, playbooks, and matrixes. These tools may be designed to facilitate the identification of a best action or choice in response to a particular situation or dilemma.