Executive Assistant to the CEO

About It Takes A Village Family of Schools (ITAV)

It Takes A Village Family of Schools (ITAV) is a beacon for educating and uplifting Black children and families across Chicago. We provide a culturally responsive, social justice–centered education that empowers students to become confident learners, critical thinkers, and changemakers.

At ITAV, learning is joyful and transformative, teaching is innovative, and classrooms extend far beyond four walls. We are committed to nurturing the whole child—academically, socially, and emotionally—while building strong, connected communities.

Position Overview

We are seeking a highly skilled, strategic, and proactive Executive Assistant to support the CEO of It Takes A Village Family of Schools. This role serves as a trusted partner to the CEO, ensuring seamless day-to-day operations, effective communication, and execution of organizational priorities.

The Executive Assistant will manage complex scheduling, coordinate high-level meetings, support cross-functional initiatives, and handle sensitive information with the highest level of professionalism and discretion. This position plays a critical role in increasing the CEO’s effectiveness and advancing ITAV’s mission and strategic goals.

Key Responsibilities

Executive Support & Calendar Management

• Manage the CEO’s calendar, including scheduling meetings, prioritizing commitments, and coordinating travel
• Ensure efficient use of time by aligning calendar with organizational priorities
• Prepare daily briefs, agendas, and materials to support CEO readiness

Communication & Coordination

• Serve as a primary point of contact for internal and external stakeholders on behalf of the CEO
• Draft, review, and manage correspondence, presentations, and reports
• Coordinate communication across departments, leadership, and external partners
• Handle confidential and sensitive information with discretion

Meeting & Board Support

• Coordinate and attend executive, leadership, and board meetings
• Prepare agendas, presentations, and supporting materials
• Capture meeting notes, track action items, and ensure follow-through
• Support preparation for high-level engagements, presentations, and public appearances

Project & Initiative Management

• Support execution of strategic initiatives and special projects led by the CEO
• Track progress, deadlines, and deliverables across departments
• Identify potential challenges and proactively propose solutions
• Maintain organized systems for project tracking and documentation

Stakeholder & Relationship Management

• Build and maintain relationships with board members, partners, donors, and community stakeholders
• Support preparation of materials for stakeholder meetings and engagements
• Manage contact lists and track key interactions for follow-up

Operations & Administrative Support

• Manage expense reports, invoices, and administrative processes related to the CEO’s office
• Coordinate logistics for events, meetings, and organizational functions
• Streamline systems and processes to improve efficiency and workflow
• Provide support to other executive team members as needed
• Perform additional duties as assigned to support organizational priorities

Why Join ITAV?

Make an Impact : Work directly with executive leadership to drive organizational success and mission impact

Grow Your Career: Gain exposure to high-level strategy, leadership, and organizational operations

Be in Community: Join a passionate, mission-driven team committed to equity and excellence

Innovate in Education: Support a forward-thinking organization transforming education and community outcomes

Position Details

• Location: Bronzeville Campus (Chicago, IL)
• Position Type: Full-Time, 12-Month Position
• Salary Range: $46,360 – $61,903
• Grant Funded
  • This position is supported through grant-funded programs that are integral to ITAV’s early childhood education model. These funding streams enable us to expand access to high-quality, culturally responsive care and learning across our communities.

Required 

• Associate's degree in a related field
• Minimum of 2 years of experience as an Executive Assistant or in a similar role supporting senior leadership
•  Exceptional organizational and time-management skills
• Strong written and verbal communication skills
• High level of discretion and professionalism in handling confidential information
• Ability to manage multiple priorities in a fast-paced environment

Preferred:

• Bachelor’s degree in a related field
• Experience supporting a CEO or C-suite executive
• Proficiency in Microsoft Office Suite and project management tools (e.g., Asana, Slack, Zoom)
• Experience in education, nonprofit, or mission-driven organizations

Who You Are

• Highly Organized: You excel at managing complex schedules and competing priorities
• Proactive & Strategic: You anticipate needs and solve problems before they arise
• Detail-Oriented: You ensure accuracy and quality in all work products
• Relationship Builder: You communicate effectively and build trust with diverse stakeholders
• Mission-Aligned: You are passionate about culturally responsive education and social justice

Compensation & Benefits

We believe in investing in our educators through a competitive, transparent compensation and benefits package designed to support your well-being, growth, and long-term success.

• Up to 80% employer-paid medical coverage
• Full benefits package, including Dental, Vision, Legal Services, and Short-Term Disability
• 3% 401(k) employer match to help you build long-term financial security
• Up to $10,000 annually in tuition assistance to support degree completion and credential advancement
• Robust paid time off,  including 16 PTO days per year, 9 sick/personal days per year, and compensatory time eligible
• 15 paid holidays annually
• Clear pathways for career advancement and leadership opportunities

Ready to Make a Difference?

If you are passionate about early childhood education and leadership and ready to make a meaningful impact, we encourage you to apply. Submit your resume and cover letter to join a team that is shaping the future—one child at a time.

Salary : $46,360 - $61,903