Executive Assistant to the Head of School

• Type: Full-Time, 12-month
• Supervisor: Head of School
• Location: Chicago, IL, on-site
• Starting Date: March, 2025

Why become part of Catherine Cook School?

Cook is a vibrant and inclusive learning community where everyone is learning and curiosity, connection, and compassion are at the heart of everything we do. We are dedicated to developing creative, collaborative problem solvers who tackle global challenges from multiple perspectives. Our dedicated faculty and staff help students from preschool (3 yrs) through 8th grade become empowered learners and leaders.

All Cook employees are trained and supported in incorporating wellness and belonging into their work with students and adults.  Diversity, equity and inclusion (DEI) and social-emotional learning (SEL) are the cornerstones upon which we build a curriculum and community.  At Cook, we commit to all community members being active learners, from our preschool students to us as adults. 

We invite you to consider how Cook will benefit from having you, along with your experiences in educating and learning, as a part of our community.  

How will this role contribute to the growth of the Cook community?

A highly competent Executive Assistant is instrumental in the Head of School achieving goals. Their service as a trusted advisor and strategic partner helps drive the school’s success.

How will I contribute and grow personally and professionally in this role?

• Connecting with and caring for colleagues and external stakeholders through weekly duties and administrative tasks 

• Growing as a life-long learner through active participation in meetings and professional development opportunities

• Growing our culture of belonging and wellness through active participation in DEI and SEL efforts 

• Serving as an Ambassador for our Enrollment Management and Development efforts

• Employing Google and Outlook Applications for individual and team collaboration and communication 

What will the ideal candidate for this role embody?

The Executive Assistant is a key partner with the Head of School. A highly organized and critical thinker who offers perspectives, ideas, and interacts with all constituents with a high level of professionalism. Based on the nature of the work and the office, the Executive Assistant is entrusted with confidential and sensitive information, requiring discretion, sound judgment, and close communication with the Head of School.

The ideal candidate will have a positive approach and the ability to learn quickly. They must be able to work efficiently and under pressure at times, handling a wide range of activities and confidential matters with discretion. This is an ideal opportunity for an accomplished and motivated Executive Assistant who is detail-oriented and enjoys working collaboratively in a fast-paced environment. The Executive Assistant will be forward-facing with members of the community and should embrace the nuances of interpersonal communication across many constituencies.

• Strategic Partnership

• Proactively anticipate the Head of School’s needs and address potential challenges.

• Provide high-level strategic counsel and support on key initiatives.

• Build and maintain strong relationships with every division and department of the school along with external stakeholders.

• Embody and communicate the school’s mission and values and manage confidential situations with discretion, respect, and sensitivity.

• Demonstrate flexibility and availability beyond standard business hours as needed to align with the Head of School’s schedule and school events.

• Strategic Support

• Regularly manage special projects and track work others are providing to the Head of School and follow up as needed.

• Conduct research and gather information as needed to support the Head of School’s decision-making.

• Identify and proactively address potential challenges and develop effective solutions.

• Communication and Correspondence

• Oversee and coordinate communications and scheduling with the Board of Trustees, including collection and distribution of materials.

• Assist with Head of School messages and branding by coordinating with internal and external communications, ensuring they are on point and in the Head’s tone.

• Draft, edit, and proofread confidential and sensitive documents.

• Administrative Support

• Manage the Head of School’s complex schedule, including meetings, travel, and events.

• Coordinate travel logistics, including flights, accommodations, and transportation while processing and reconciling expenses.

• Maintain accurate and confidential records, including contact information, meeting notes, and important documents.

What else is there to know about employment at Cook?

Catherine Cook offers a comprehensive benefits package designed to support the well-being and financial security of our employees. Benefits for full-time eligible employees include:

• Medical, dental, and vision coverage

• 403(b) plan

• 100% of the premium covered for Basic Life insurance, STD, LTD, AD&D

• HRA, HSA, FSA, Dependent Care available

• Professional Development opportunities

• Generous paid time off

• Lunch provided during the school year

• Pet Insurance

• Identity Theft Protection

In compliance with IL’s Equal Pay Act, the salary range for this position is $55,000-$70,000

Ultimately, in determining your pay, a variety of factors including your key skills and other job-related factors, including peer equity, market, and organizational elements are considered, among others.

Catherine Cook School is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Salary : $55,000 - $70,000