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Associate Director of Employment and Education

A SAFE HAVEN LLC
Chicago, IL Full Time
POSTED ON 4/18/2026
AVAILABLE BEFORE 6/17/2026

Position Summary

The Associate Director of Employment and Education is a senior operations and performance management role responsible for driving measurable outcomes across A Safe Haven’s workforce development and education portfolio. This position leads the day-to-day execution of a multi-grant department, managing budgets, compliance obligations, staff performance, and a robust data infrastructure to ensure the department consistently meets or exceeds contractual deliverables.

The Associate Director functions as an operational executive within the Programs division — building the systems, accountability structures, and employer relationships necessary to generate reliable employment outcomes and advance economic mobility for program participants. This role is a critical link between housing stability goals and income attainment, ensuring individuals have the financial capacity to achieve and sustain permanent housing.

Key Responsibilities

Department Operations & Execution

• Oversee daily operations of the Employment and Education department, ensuring efficient workflows, consistent service delivery, and a high-performance culture across all program functions.

• Translate organizational and funder goals into actionable execution plans, staff priorities, and measurable performance targets.

• Design, implement, and continuously improve operational systems spanning intake, assessment, job readiness, training enrollment, placement, retention, and post-placement follow-up.

• Identify and remove operational barriers through coordinated wraparound services with internal departments (housing, behavioral health, case management).

Grant Management, Budget Oversight & Compliance

• Serve as the primary manager for multiple grants funding the Employment and Education department, with accountability for contract deliverables, budget stewardship, and performance outcomes.

• Maintain grant calendars, reporting pipelines, and documentation standards; ensure all submissions are accurate, timely, and audit-ready.

• Partner with Finance to monitor expenditures, track budget variances, and support fiscal compliance across all funding streams.

• Lead preparation for funder monitoring visits, program audits, and corrective action plans; ensure sustained compliance with all funder and regulatory requirements.

• Contribute to grant renewals and funding expansions through performance narratives, outcome summaries, and program improvement documentation.

Performance Management & KPI Accountability

• Own departmental KPIs including enrollments, credential attainment, job placements, wage benchmarks, 30/60/90-day retention, and participant advancement.

• Build and manage performance dashboards, scorecards, and team accountability routines (pipeline reviews, case conferences, employer tracking meetings).

• Ensure timely and accurate data entry across all required systems and databases; maintain strong data integrity for funder reporting and internal decision-making

• Translate performance data into actionable insights, driving continuous improvement in program design, staffing, and resource allocation.

• Produce internal leadership reports and support outcome storytelling for funders, partners, and organizational stakeholders.

Staff Supervision & Team Development

• Directly supervise employment and education staff, including employment coaches, job developers, retention specialists, vocational training coordinators, adult education staff, and contractors.

• Set clear performance expectations, caseload standards, and accountability benchmarks; deliver consistent coaching, performance feedback, and professional development.

• Lead hiring, onboarding, and workforce planning to ensure staffing continuity and service delivery quality at all times.

• Foster a high-standards, mission-aligned team culture grounded in accountability, equity, and dignity for participants.

Employer Partnerships & Placement Strategy

• Build and manage a strategic employer pipeline to generate reliable, quality job placements and long-term retention outcomes for program graduates.

• Set and monitor job development and employer engagement standards, including outreach targets, relationship management protocols, and sector-specific strategies.

• Coordinate hiring events, employer site visits, and recruitment partnerships aligned with in-demand industry sectors.

• Collaborate with employer partners to address retention challenges and develop advancement pathways for placed participants.

Vocational Training & Education Oversight

• Provide operational oversight of vocational training and adult education programming, ensuring offerings align with labor market demand and defined career pathways.

• Manage and evaluate instructors and training vendors against performance standards for attendance, completion, and credential attainment rates.

• Partner with the VP of Operations to align trainee engagement with A Safe Haven’s social enterprise initiatives.

• Monitor training-to-employment pipeline performance and adjust programming, scheduling, and participant supports to maximize completion and placement rates.

Cross-Functional Collaboration & External Representation

• Partner with housing, shelter, behavioral health, and case management leadership to align employment services with individual stability and housing retention plans.

• Represent the Employment and Education department in internal leadership meetings, cross-functional planning, and case conferences.

• Represent A Safe Haven externally in funder meetings, workforce system convenings, and community partner coalitions as needed.

Qualifications:

Education

• Bachelor’s degree required.

• Master’s degree preferred in business administration, public administration, nonprofit management, social work, or a related field.

Experience

• 5 years of progressive experience in program management, workforce development, employment services, or a related human services field.

• 3 years of supervisory or team leadership experience, with a demonstrated track record of managing staff to performance outcomes.

• Demonstrated experience managing grant-funded programs, including budget oversight, performance reporting, and compliance.

• Experience working with populations impacted by homelessness, justice involvement, behavioral health challenges, or other barriers to employment strongly preferred.

Technical Skills

• Strong proficiency in data analysis, performance reporting, and dashboard management; advanced Excel skills required.

• Experience with CRM or case management databases (e.g., Salesforce, ETO, Apricot, or similar).

• Demonstrated ability to manage multi-funder grant portfolios and coordinate with finance on budget tracking and variance analysis.

 

Core Competencies

✓ Operational Leadership & Execution ✓ Grant & Financial Management

✓ KPI Accountability & Data-Driven Decision Making ✓ Staff Supervision & Performance Coaching

✓ Employer Engagement & Pipeline Development ✓ Cross-Functional Collaboration

✓ Written & Verbal Communication ✓ Equity-Centered & Mission-Driven Practice

 

Work Environment & Requirements

• Primarily onsite at A Safe Haven program locations, with local travel to employer partners, training sites, and community meetings.

• Occasional evenings or weekends required to support hiring events, program graduations, or urgent operational needs.

• Must be able to pass all required background checks applicable to the role.

Salary : $75,000 - $95,000

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