Pay for Student Success Act This bill amends the Higher Education Act of 1965 to require the Department of Education (ED) to contract with eligible entities for pay-for-success projects that develop, implement, evaluate, and promote innovative strategies for increasing the postsecondary education retention and completion rates of students who receive Pell Grants and first-generation postsecondary students. Each entity that receives a contract must provide 90% of the project costs up front. ED may reimburse an entity for no more than 75% of the total project costs if ED determines, based on an independent evaluation, that the project is successful.