Weissman has nearly 20 years of experience at MDRC directing projects, providing technical assistance, conducting qualitative research, and disseminating findings in a wide range of education and social policy settings. His current work is focused primarily in the area of postsecondary education, illuminating ways to improve college access, persistence, and success for low-income and underprepared students. Weissman is currently leading Aid Like A Paycheck, a project testing the impacts of innovative changes to financial aid disbursements. His work on developmental education includes helping to launch an evaluation of developmental math pathways as part of the Center for the Analysis of Postsecondary Readiness, and having played a vital role in the National Center for Postsecondary Research, working on the Learning Communities Demonstration and the Texas Developmental Summer Bridge Study. Weissman has also provided technical assistance, designed and launched evaluations, and conducted qualitative research in a range of other social policy areas, including early childhood education, maternal and infant well-being, job training and parenting programs for noncustodial parents, public housing, and welfare employment programs.