Bailey is Dean Emeritus at the GSSWSR and Special Assistant to the College President for Community Partnerships. She is also the director of the Social Justice Initiative. Previous leadership roles include being dean of the Mandel School of Applied Social Sciences at Case Western Reserve University, and vice-president and dean and then acting president at Columbia's Teachers College. In 2006, Bailey went to the University of Minnesota as the first dean of a new multidisciplinary college. She was dean of the GSSWSR from 2009 until 2017.
Bryn Mawr's Graduate School of Social Work and Social Research (GSSWSR) is distinctive for its dedication to fine teaching, individual attention, and high academic standards within a liberal arts tradition. Founded in 1915, the GSSWSR has always embraced scholarship, practice, and collaboration within social work and social welfare.