Abstract: Methods, apparatus, and articles of manufacture to iteratively compile software to meet user-defined criteria are disclosed. A disclosed example method receives target performance characteristics from a user and compiles source code to generate object code. The object code is then analyzed to determine measured performance characteristics. The measured performance characteristics are then compared to the target performance characteristics. If the measured performance characteristics are unacceptable based on the target performance characteristics, the one of a plurality of compiler options configurations is selected based on empirical data correlating the compiler options configurations to structural characteristics of at least one of the source code or the object code.