Associate Director of Employment and Education - Chicago, IL

Position Summary · The Associate Director of Employment and Education leads day-to-day operations and performance for A Safe Haven's Employment and Education department, ensuring high-quality service delivery across job readiness, placement, retention, vocational training, and ad ...

Job description

Position Summary

The Associate Director of Employment and Education leads day-to-day operations and performance for A Safe Haven's Employment and Education department, ensuring high-quality service delivery across job readiness, placement, retention, vocational training, and adult education. This role directly manages several key grants that fund the department, drives compliance and reporting, and builds systems that strengthen outcomes and participant experience. The Associate Director supervises staff, supports cross-department coordination (housing, supportive services, behavioral health, case management), and maintains strong employer and training partnerships to advance economic mobility.

This position is specifically responsible for aligning workforce development services with supportive and permanent housing goals, ensuring residents have meaningful pathways to income so they can achieve and maintain housing stability, meet lease obligations, and build long-term self-sufficiency

Key Responsibilities

Department Operations and Leadership

• Lead daily operations of employment and education services to ensure consistent, high-quality programming and a strong participant experience.
• Translate departmental goals into clear execution plans, staff priorities, and performance targets.
• Implement and refine workflows spanning intake, assessment, job readiness, training enrollment, placement, retention, and follow-up.
• Coordinate with internal partners to remove barriers to employment through wraparound supports.

Grant Management, Compliance, and Reporting

• Manage several key grants that fund the employment and education department, including contract deliverables, budgets in coordination with finance, and performance outcomes.
• Maintain grant calendars, reporting timelines, and documentation standards; ensure submissions are accurate, on-time, and audit-ready.
• Track and report progress toward required metrics (enrollments, credentials, placements, wages, retention, measurable skill gains, etc.).
• Lead preparation for monitoring visits, audits, and corrective actions; ensure compliance with funder requirements and internal policies.
• Support grant renewals and expansions by contributing narratives, performance summaries, and program improvement plans.

Oversight of Vocational Training and Adult Education

• Provide oversight of A Safe Haven's vocational training and adult education programming (e.g., sector-based training, certifications/credentials, GED/HiSET preparation, or similar offerings as applicable).
• Ensure training and adult education offerings align with employer demand and defined career pathways.
• Partner with VP of Operations to coordinate trainee engagement in A Safe Haven social enterprises
• Manage and evaluate internal instructors to ensure quality instruction, attendance, completion, and credential attainment.
• Monitor training and education outcomes and continuously improve curriculum alignment, participant supports, scheduling, and referrals.
• Coordinate supportive services (transportation, childcare planning, uniforms/tools, etc.) that increase training completion and employment success.

Outcomes, Data, and Performance Management

• Own department performance across enrollments, training completions, credential attainment, job placements, wage targets, retention, and advancement.
• Implement dashboards, scorecards, and team routines (case reviews, pipeline meetings, employer pipeline tracking) to drive accountability.
• Ensure accurate and timely documentation in required databases and internal systems; maintain strong data integrity.
• Produce internal reporting for leadership and support outcome storytelling for partners and funders.

Staff Supervision and Team Development

• Supervise employment and education staff (employment coaches, job developers, retention specialists, vocational training coordinators, adult educators, and/or contractors).
• Set clear expectations and caseload/portfolio standards; provide coaching, performance feedback, and professional development.
• Support hiring, onboarding, training, and coverage planning to ensure continuity of service delivery.
• Promote a trauma-informed, participant-centered culture aligned with A Safe Haven's mission and values.

Employer Partnerships and Placement Strategy

• Strengthen and expand employer partnerships to create reliable hiring pipelines and improve retention outcomes.
• Guide job development strategy and employer engagement standards, including outreach targets and relationship management practices.
• Coordinate hiring events, recruitment sessions, employer site visits, and sector-based partnerships.
• Collaborate with employers to address retention challenges and create advancement opportunities for placed participants.

Cross-Functional Collaboration and Representation

• Partner with housing, shelter, behavioral health, and case management leaders to align workforce services with participant stability plans.
• Participate in leadership meetings and case conferences; represent Employment and Education in internal planning.
• Represent A Safe Haven externally in funder meetings, workforce systems convenings, and partner coalitions as needed.

Qualifications

• Bachelor's degree required.
• Master's degree preferred (public administration, social work, counseling, nonprofit management, business, workforce development, education, or related field).
• 4+ years of progressive experience in workforce development, employment services, adult education, vocational training, or related human services programming.
• 2+ years of supervisory or team leadership experience preferred.
• Demonstrated experience managing grant-funded programs, including performance reporting and compliance oversight.
• Strong knowledge of career pathways, job readiness/placement models, employer engagement, and training-to-employment pipelines.
• Experience serving individuals impacted by homelessness, justice involvement, behavioral health needs, or other barriers to employment strongly preferred.
• Strong data skills and comfort using CRMs/databases, Excel, and performance dashboards.

Skills and Competencies

• Strong operational leadership with the ability to build structure, improve systems, and maintain quality at scale.
• Grant management discipline: organized, deadline-driven, and detail-oriented with strong documentation habits.
• Ability to coach and hold accountability while maintaining a supportive, high-standards culture.
• Strong relationship-building skills with employers, education/training providers, and workforce system partners.
• Excellent written and verbal communication for funder narratives, reports, and stakeholder updates.
• Commitment to equity, dignity, and trauma-informed practice.

Work Environment and Requirements

• Primarily onsite with some local travel to employer partners, training sites, and community meetings.
• Occasional evenings or weekends to support hiring events, graduations, or program needs.
• Ability to pass required background checks as applicable to the role.