The need for educational programs to show their return on investment is exemplified in the intense debate surrounding gainful employment programs--defined as programs that lead to gainful employment in a recognized occupation and theoretically differ from programs that offer education in the liberal arts or prepare students for further education. Through the negotiated public rulemaking process, the U.S. Department of Education sought to operationalize the phrase "gainful employment" in the Higher Education Act of 1965 with metrics that tie institutional eligibility for federal student aid to work-related outcomes of students from certain educational programs. Given the focus on labor market outcomes of students as exemplified in gainful employment debate and, perhaps more importantly, the policy proposition that a more educated population will in turn lift the nation out of the current great recession, this chapter depicts the complexities, opportunities, and challenges in aligning workforce and education data. To accomplish this task, the chapter examines the sources of workforce data available, describes workforce metrics currently in use and those considered to measure program effectiveness and justify program costs, and closes with a discussion of the challenges inherent in connecting education and workforce data. (Contains 2 tables.)