Clarkson University is home to a 30-year-old, graduate-level teacher education program which includes a student teaching placement. The placement process is one of the most time consuming aspects of the work done in the teacher education program. In order to minimize time spent placing student teachers and increase the level of service provided to those who require additional assistance, the teacher education program designed a prototype optimization software system to match student teachers with mentors. This optimizer is based on programming principles used in popular software applications individuals might use to find a relationship match. Rather than matching individuals for dating purposes, this model matches individuals based on their student teaching attributes. The software considers student teacher preferences, experience, and academic performance. It also accounts for factors related to mentors such as teaching experience, mentoring experience, school setting, and location. In an initial demonstration, the prototype software was tested with a sample of five student teachers and compared to the actual placement decisions made by the program faculty. The initial results showed strong agreement with the decisions made by program faculty. The research team used the Participatory Action Research process to tackle an adaptive problem that required many sets of expertise and an iterative research cycle. This article includes the results of this project along with challenges experienced in its development and next steps.