Associate Director of Reentry and Student Success

About the role

The Center for Prison Education (CPE) at Wesleyan University is seeking an Associate Director of Reentry and Student Success to lead the expansion of educational opportunities for formerly incarcerated students. Founded in 2009, CPE provides rigorous liberal arts education and degree opportunities to students at Cheshire Correctional Institution and York Correctional Institution. Over the past sixteen years, CPE has expanded educational access and built a community of students, graduates, and alumni.

Responsibilities

• Develop and implement CPE’s academic reentry and student success strategy.
• Build relationships with students preparing for release and provide individualized educational planning and transition support.
• Serve as the primary campus navigator for BLS Degree Completion Scholars and support their transition into academic and student life at Wesleyan.
• Aid students in navigating admissions, transfer, enrollment, financial aid, and degree-completion processes at Wesleyan, Connecticut State Community College, and other institutions.
• Coordinate academic and student support services related to educational persistence, academic success, and degree completion.
• Maintain regular contact with students and alumni pursuing educational goals and provide coaching and guidance.

Community Building and Alumni Support

• Develop and sustain community-building and alumni programming for the Center for Prison Education community.
• Organize alumni gatherings, professional development programs, networking opportunities, and community-building events.
• Recruit, train, and supervise CPE’s Alumni Engagement Fellows, rotating yearlong roles serving as community liaisons and peer reentry mentors from the CPE alumni network.
• Create opportunities for alumni leadership, public engagement, storytelling, and participation in Center activities.
• Support the development and maintenance of an alumni network.

Partnerships & Opportunity Development

• Build and maintain relationships with educational institutions, employers, workforce development programs, community organizations, and reentry service providers throughout Connecticut.
• Identify and expand pathways to continued education, professional certifications, internships, employment, and civic engagement.
• Coordinate with Wesleyan offices, faculty, and staff to strengthen institutional support for formerly incarcerated students.
• Represent CPE in local, state, and national conversations related to higher education in prison, academic reentry, and post-release student success.

Program Development, Assessment, and Stewardship

• Manage the alumni engagement and reentry support budget, submitting expense documentation in line with CPE policies, grant requirements, and Wesleyan financial procedures.
• Contribute to reporting, data collection, and evaluation for the three-year CDS grant and required federal PEP outcome reports, in coordination with CPE's Director and Wesleyan's Office of Financial Aid.
• Maintain program documentation, process guides, resource lists, and student-facing materials.

Administration and Program Support

• Manage direct-support programs that assist students and alumni in pursuing educational and professional goals.
• Maintain systems for tracking educational progress, student engagement, and post-release outcomes.
• Contribute to strategic planning, program assessment, grant reporting, and continuous improvement efforts.
• Collaborate with CPE staff to ensure continuity of support from enrollment in prison through post-release educational and professional goals.

Continuity of Student Support

• Work closely with the Associate Director of Programs and CPE staff to ensure students experience consistent support from enrollment through release and into the community.
• Contribute to pre-release planning and the development of individualized pathways connecting students to post-release educational, employment, and community resources.
• Collaborate in the delivery of pre-release workshops and informational sessions on topics including financial aid, college transfer, disclosure of conviction history, digital skills, and community resources at CPE's correctional sites and through other program formats as appropriate.