Abstract: A computer-implemented system and method for modeling contractual terms as structured data for license compliance analysis is provided. A set of electronically-stored expressions is defined. Each expression includes parseable contract terminology and a meaning associated with the contract terminology. A license for a product is converted into structured data. Terms of use included in the license are parsed. The parsed terms of use are matched against the parseable contract terminology in the set of expressions. For each expression whose parseable contract terminology was matched to a parsed term of use, the associated meaning is assembled into a schematized data structure that represents the product license. Compliance of an installed base of the product is evaluated against each meaning in the schematized data structure.