Associate Director of Reentry and Student Success

Wesleyan University•Middletown, CT

1d•Onsite

About The Position

Founded in 2009, Wesleyan University’s Center for Prison Education (CPE) provides rigorous liberal arts education and degree opportunities to students at Cheshire Correctional Institution and York Correctional Institution. More than 180 students have participated in CPE courses, and more than 80 have earned college credentials through partnerships with Wesleyan University and Connecticut State Community College. Over sixteen years, the Center has expanded educational opportunities for incarcerated learners while building a community of students, graduates, and alumni. In 2025–26, Wesleyan launched the Bachelor of Liberal Studies (BLS) Degree Completion Scholars Program, creating a pathway for former CPE students to continue their education on Wesleyan’s campus. Through small annual cohorts, the program extends the reach and power of Wesleyan affiliation beyond prison walls, supporting students on the continuum from in-prison education to campus integration. CPE is also deepening its commitment to the broader community of students and alumni returning home after incarceration. Since the Center’s founding, more than 80 students who began their studies through CPE have returned to communities across Connecticut. As part of its next chapter, CPE is developing a comprehensive reentry and student success strategy that supports students pursuing a wide range of educational and professional pathways. These include degree completion at Wesleyan, transfer and enrollment at Connecticut State Community College and other institutions, workforce and professional certification programs, entrepreneurship, public service, and community leadership. The Center seeks to build a durable network of relationships, resources, and opportunities that enables former students to remain connected to educational institutions, professional communities, and one another. Reporting to the Director of the Center for Prison Education, the Associate Director of Reentry and Student Success will lead this emerging area of the Center’s work. The Associate Director serves as the primary point of contact for students transitioning from incarceration to community life and for CPE alumni pursuing continued education, employment, leadership opportunities, and professional growth. Working across Wesleyan University and with partners throughout Connecticut, the Associate Director will design and implement programs that strengthen educational continuity after release, cultivate a strong and connected community of former students, expand educational and professional pathways, and connect students and alumni with the resources necessary to achieve their goals. The position is critical to ensure that the educational journeys begun in the CPE classrooms continue to generate opportunity, belonging, and impact long after release.

Requirements

Bachelor's degree and a minimum of five years of experience in reentry support, student services, or related work; or an equivalent combination of education, training, and experience.
Ability to build and maintain relationships with people from a wide range of backgrounds, including currently and formerly incarcerated individuals.
Experience providing advising, case management, or navigation support to individuals facing significant barriers, including support with college admissions, financial aid, or transfer processes.
Familiarity with community reentry resources in Connecticut or demonstrated ability to quickly develop this knowledge upon hire.
Effective communication skills, with the ability to work effectively with students, faculty, administrators, community partners, and correctional staff.
Organizational skills and ability to manage multiple projects, deadlines, data systems, and compliance requirements at the same time.
Demonstrated commitment to educational access and student success.
Ability to handle sensitive and legally protected student information with discretion, consistent with FERPA.
Proficiency with Microsoft Office and willingness to learn Wesleyan systems including Workday, Moodle, and Wes Maps, and student records or case tracking tools.
Must be at least 20 years of age and possess a valid U.S. driver’s license for a minimum of three years with a satisfactory driving record, as required for vehicle insurance eligibility.
Ability to travel to program sites and partner locations across Connecticut.
Availability to work some evenings and weekends as program activities required.

Nice To Haves

Familiarity with the barriers facing individuals returning from incarceration through professional, volunteer, community-based, or direct lived experience.
Master's degree in social work, counseling, higher education administration, public policy, criminal justice, or a related field.
Experience working in correctional or other high-security institutional settings.
Experience building or managing alumni engagement, mentorship, or community programs.
Ability to obtain required clearances for work at Connecticut correctional facilities ; must be at least 21 years of age as required for CTDOC facility entry.
Experience with grant-funded programs, including outcome tracking, reporting, and compliance documentation.
Experience supervising volunteers, student workers, or part-time staff.
Experience presenting at conferences or contributing to field-level work in higher education in prison or educational equity.

Responsibilities

Lead the development and implementation of 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.
Assist 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.
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.
Design and oversee peer mentorship initiatives connecting current students, recently released students, and alumni.
Create opportunities for alumni leadership, public engagement, storytelling, and participation in Center activities.
Support the development and maintenance of an alumni network.
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.
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.
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.
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.
Build relationships with currently enrolled CPE students -- as appropriate and consistent with correctional facility access requirements -- particularly those approaching release, working collaboratively with CPE staff to understand each student's academic progress, goals, strengths, and anticipated reentry needs.
In partnership with the Associate Director of Programs and other CPE staff, 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.
Other duties as assigned.