Job Description

Our client is seeking a Deputy Director who will provide strategic and operational leadership for a federally funded early childhood education program. This role oversees day-to-day program implementation, compliance, staff supervision, and long-term planning, ensuring alignment with Head Start Performance Standards as well as federal, state, and local regulations.

Working closely with senior leadership, the Deputy Director is responsible for cultivating a collaborative and high-performance environment, maintaining effective partnerships, and representing the organization across regional and national platforms. The position requires regular travel throughout Chicago and surrounding areas to support agency sites and stakeholders.

Key Responsibilities:

• Lead program operations and ensure compliance with Head Start regulations, state licensing standards, and other grant requirements.
• Oversee fiscal planning and management, including budget development and in-kind contributions, in partnership with finance staff.
• Supervise a team of Assistant Directors across key domains (education, health, family engagement, professional development).
• Support policy governance by collaborating with the Policy Council and preparing necessary reports and updates.
• Guide the implementation and ongoing improvement of operational systems, policies, and procedures.
• Monitor curriculum fidelity, assessments, and overall classroom quality across settings, including center-based, home-based, and partner agencies.
• Foster collaboration with internal teams to improve communication and strengthen services for children and families.
• Represent the program at community, state, and national meetings or events; promote visibility and advocacy initiatives.
• Contribute to performance reporting, grant deliverables, and continuous improvement planning.
• Maintain relationships with local service providers and community organizations to expand family support resources.

Required Qualifications:

• Master’s degree in education or a related field
• 6+ years of progressive leadership experience in early childhood education, including Head Start
• Demonstrated success in managing complex operations in a multi-site, compliance-driven environment
• Strong background in supervision, coaching, and staff development
• Experience working with performance standards, regulatory guidelines, and fiscal oversight
• Ability to interpret policy, develop systems, and evaluate impact
• Excellent written and verbal communication skills; effective with diverse populations
• Skilled in change management, conflict resolution, and team building

Preferred Qualifications:

• Familiarity with Paylocity or a similar HRIS
• Knowledge of budgeting processes and federal grants
• Previous experience leading within a matrixed or shared services environment
• Strong understanding of family engagement frameworks and inclusive education practices

Why choose Addison Group?

• Pay: We negotiate high salaries using the US Bureau of Labor Statistics
• Benefits & Bonuses: You are eligible for medical, dental, vision insurance benefits, 401K, and monetary bonuses
• Permanent Employment: Many of Addison’s Administrative job openings lead to potential permanent employment
• Connections: You connect directly with hiring managers from renowned organizations
• Options: You are presented with multiple employment options near your home
• Professional Development: You are provided with hiring process advice, resume revision, and employment term negotiation

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities upon request.

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