Assistant Director, Re-Entry Services

Project H.O.O.D.; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Job summary

Project H.O.O.D. seeks an experienced Re-Entry Services Assistant Director to lead day-to-day operations of the re-entry program in Chicago. You will supervise coordinators, manage cohort delivery, ensure accurate data entry, and prepare compliance-ready records for monitoring and audits.

You will oversee training, performance management, and collaboration with housing, legal, behavioral health, and workforce partners to support participant completion and placement targets.

Qualifications

• Bachelor's degree or equivalent experience in a related field.
• 4+ years in re-entry, violence prevention, workforce development, or human services.
• At least 1 year supervising staff.
• Experience with formal performance reporting and compliance documentation.
• Strong data discipline and data-entry accountability.
• Excellent written and verbal communication; ability to work evenings/weekends as cohort schedules require.

Responsibilities

• Oversee day-to-day delivery of re-entry services across intake, case management, cohorts and employment placement.
• Schedule and launch four six-week cohorts; coordinate facilitators, spaces and materials.
• Monitor caseload distribution and rebalance assignments for 15–20 participants per coordinator.
• Troubleshoot service-delivery issues and support frontline staff.
• Supervise Re-Entry Coordinators and Workforce Case Manager; conduct supervision.
• Lead weekly case conferencing and performance reviews; onboard new staff.
• Support hiring decisions and personnel actions with HR; uphold program standards.
• Maintain confidentiality and audit-ready program and participant records.

Skills

People management

Data discipline

Communication

Time management

Team leadership

Problem solving

Education

Bachelor's degree in social work, criminal justice, public administration, human services, or related field

Master's degree preferred

Job description

Company Description Project H.O.O.D. is a 501(c)(3) organization founded in 2012 to empower individuals with the tools, information, and guidance needed to become peacemakers, problem solvers, leaders, and entrepreneurs in their communities. Inspired by the “Rooftop Pastor” Corey Brooks’ 94-day advocacy effort to draw attention to gun violence on Chicago’s South Side, the organization focuses on ending violence and building stronger neighborhoods. Its programs serve youth, adults, and families, providing resources, skills, and experiences that support healthy, successful, and upward mobility. Project H.O.O.D. emphasizes empowerment over enablement and seeks to be a leader in innovation and transformation in the Englewood and Woodlawn communities.

Position Summary The Re-Entry Services Assistant Director is the operational lead of the Re-Entry program. The Re-Entry Program Director sets direction and manages external relationships; the Assistant Director ensures that day-to-day services run effectively, cohorts launch on schedule, caseloads remain covered, data is entered accurately and on time, and program records remain ready for monitoring and audit review. This position directly supervises the part-time Re-Entry Coordinators and the Workforce Case Manager and serves as acting lead in the Program Director's absence. The Assistant Director is accountable for supporting achievement of the program's participant completion, placement, and retention targets.

Program Operations

• Manage day-to-day delivery of re-entry services across intake, case management, cohort training, and employment placement.
• Schedule and launch four six-week cohort cycles, coordinating facilitators, space, materials, and participant recruitment.
• Monitor caseload distribution and rebalance assignments to maintain service quality across approximately 15 to 20 participants per coordinator.
• Troubleshoot service-delivery breakdowns and remove barriers for front-line staff.
• Directly supervise the Re-Entry Coordinators and the Workforce Case Manager.
• Lead weekly case conferencing and individual supervision.
• Onboard and train new re-entry staff, set performance expectations, provide ongoing coaching, and conduct performance reviews.
• Participate in hiring, performance management, corrective action, development, and separation processes for assigned staff and make recommendations to the Re-Entry Program Director and Human Resources regarding personnel actions.
• Build a team culture consistent with Project H.O.O.D.'s principle-based management approach.

Data Reporting & Program Compliance

• Own the accuracy and timeliness of participant data in the program's system of record.
• Prepare quarterly and annual performance reports in coordination with the Re-Entry Program Director and finance staff.
• Serve as the program's point of contact for monitoring visits, site visits, and audit requests.
• Maintain files, consents, and documentation to funder standards and correct gaps before they become findings.
• Ensure the program operates within the approved budget narrative, program scope, and applicable funder requirements.
• Ensure participant completion incentives, CTA cards, and supportive services are issued and documented within funder rules, including prior approval for purchases over $100.
• Track spending against personnel, supplies, and participant incentive budget lines and promptly flag variances to the Re-Entry Program Director.
• Maintain audit-ready documentation across participant, program, personnel, and expenditure records and promptly elevate program-compliance risks to the Re-Entry Program Director and Chief Operating Officer.
• Maintain the confidentiality, privacy, accuracy, and security of participant, employee, program, and organizational information in accordance with Project H.O.O.D. policies, funder requirements, and applicable law.

Partnerships

• Manage working relationships with housing, legal, behavioral health, and workforce partners.
• Coordinate contracted expungement legal services and life-skills facilitation scopes.
• Represent the program with courts, parole and probation agencies, and community partners as assigned.

Qualifications

Required

• Bachelor's degree in social work, criminal justice, public administration, human services, or a related field; equivalent experience will be considered.
• Four or more years of experience in re-entry, violence prevention, workforce development, or human services, including at least one year supervising staff.
• Demonstrated experience managing a program with formal performance reporting and compliance documentation.
• Strong data discipline, including the ability to hold a team accountable for timely and accurate data entry and to interpret outcome data critically.
• Excellent written and verbal communication skills with participants, funders, and partners.
• Ability to work some evenings and weekends aligned with cohort and participant schedules.

Preferred

• Master's degree in social work, public administration, or a related field.
• Lived and/or professional experience working with individuals, families, or communities impacted by the criminal legal system.
• Established relationships across Chicago South Side re-entry, legal, and employer networks.
• Training in trauma-informed supervision or clinical supervision.