Exec Admin Assistant to the Chief Administrator of Education

Oak Hill has been enhancing the lives of people with disabilities since 1893! We invite you to join our team of highly committed professionals. Founded in 1893 by trailblazer and visionary, Emily Wells Foster, Oak Hill has over 129 years of experience providing the highest quality services to people with varying disabilities. Oak Hill sets the standard, partnering with people with disabilities, to provide services and solutions promoting independence, education, health, and dignity.

Executive Assistant to the Chief Administrator

Oak Hill Schools
Are you a strategic, detail-driven professional who thrives in a fast-paced, mission-centered environment? Do you excel at managing complex priorities while maintaining the highest level of discretion and professionalism?
Oak Hill Schools is seeking a dynamic Executive Assistant to the Chief Administrator to serve as a trusted partner, operational leader, and central office anchor supporting our educational mission for students with disabilities.

Why This Role Matters
This is more than an administrative role — it’s a mission-critical position that directly supports student success.

As the Executive Assistant, you will:

• Serve as a strategic partner to the Chief Administrator
• Oversee central office operations and front office management
• Ensure compliance with state regulations and accreditation requirements
• Support initiatives that sustain and grow student enrollment
• Help create an environment where classrooms remain focused on learning and achievement

Your work enables leadership to focus on advancing educational excellence and reinforcing dignity and lifelong learning opportunities for students.

What You’ll Do
Executive & Strategic Support

• Manage a complex and high-priority executive calendar
• Prepare confidential reports, correspondence, presentations, and executive communications
• Record and distribute meeting minutes
• Provide real-time advisory support regarding policy, regulatory, and operational decisions
• Supervise the Administrative Assistant

Operational Leadership

• Oversee central office workflow and streamline administrative processes
• Maintain accurate records including student enrollment data
• Support strategic initiatives aimed at increasing student referrals and census
• Coordinate school-wide calendar planning and department scheduling

Compliance & Accreditation

• Maintain accreditation and oversee attestation/re-accreditation processes
• Ensure compliance with State agency regulations and internal reporting requirements
• Manage purchase orders, invoices, vendor billing compliance, and cost controls
• Oversee department inventory and employee equipment distribution/return

Communication & Stakeholder Management

• Serve as liaison between Oak Hill Schools, public school districts, families, staff, and community partners
• Draft professional and confidential communications including reports, notifications, payroll inquiries, and personnel transactions
• Manage emergency communications and telecommunications alerts when necessary
• Greet and engage stakeholders with professionalism and discretion

Technology & Process Improvement

• Utilize Microsoft Outlook, Excel, PowerPoint, and emerging platforms to organize and leverage data
• Develop efficient systems for document management and data retrieval
• Improve workflows to enhance operational effectiveness across departments

What Success Looks Like

• Seamless executive support that maximizes leadership productivity
• Accurate reporting and documentation ensuring regulatory compliance
• Streamlined processes that improve central office efficiency
• Strong stakeholder relationships built on professionalism and trust
• Sustained or increased student census aligned with organizational goals

What You Bring

• Strong executive-level administrative experience
• Exceptional discretion and independent judgment
• Advanced proficiency in Microsoft Office Suite
• Experience managing confidential information
• Ability to prioritize competing demands in a fast-paced environment
• Strong analytical and problem-solving skills
• Excellent written and verbal communication skills

We support equality for and advancement of all people, based on their qualifications and actions alone, without regard to color, gender, age, religion, national origin or disability.

Our company is dedicated to fostering an inclusive environment. If you need a reasonable accommodation to participate in the job application or interview process, please reach out to total.rewards@oakhillct.org. We will make every effort to accommodate your needs in accordance with applicable laws and our commitment to accessibility and inclusion.

An Equal Opportunity Employer.