Pennwood Cyber Charter School - Executive Assistant

The Executive Assistant serves as a trusted partner to the CEO and senior leadership team, providing executive support while driving operational excellence, compliance, process improvement, and organizational effectiveness initiatives. This role bridges executive administration with strategic operational coordination by managing leadership workflows, developing and maintaining standard operating procedures, supporting compliance efforts, overseeing reporting systems, and leading continuous improvement initiatives across the school.

The ideal candidate is highly organized, analytical, and proactive, with the ability to manage executive priorities while supporting schoolwide operational systems, compliance requirements, and cross-departmental initiatives.

Key Responsibilities

Executive & Leadership Support

Manage the CEO’s calendar, scheduling, priorities, and communications to maximize organizational effectiveness.

Coordinate leadership meetings, agendas, presentations, materials, and follow-up action items.

Serve as a primary liaison between executive leadership and internal/external stakeholders.

Prepare reports, presentations, summaries, and correspondence for leadership meetings and organizational communications.

Support strategic planning efforts and leadership initiatives through project coordination and operational follow-through.

Organizational Operations & Process Improvement

Develop, document, implement, and maintain school-wide standard operating procedures (SOPs).

Partner with department leaders to evaluate workflows and identify opportunities for increased efficiency and consistency.

Lead and support continuous improvement initiatives and operational excellence projects.

Analyze operational data and trends to identify gaps, risks, and opportunities for improvement.

Assist with organizational change management efforts, including communication, implementation, and staff adoption.

Compliance & Reporting

Support compliance with Pennsylvania Department of Education (PDE) requirements, school policies, and operational regulations.

Coordinate compliance tracking, documentation management, and audit readiness activities.

Support state reporting processes, including data collection, validation, tracking, and submission timelines.

Data Management & Organizational Effectiveness

Support data integrity through standardized reporting practices and consistent tracking methodologies.

Provide data analysis and operational insights to support leadership decision-making.

Create resources, training materials, and documentation that improve staff understanding and utilization of systems and processes.

Board Governance & Administrative Operations

Coordinate Board of Trustees meeting logistics, materials, records, and communications.

Maintain confidential organizational, leadership, and employee records in accordance with legal and organizational requirements.

Support HR-related operational initiatives and staffing processes as needed.

Manage organizational documentation systems and records retention practices.

Core Competencies

Organizational Excellence

Demonstrates exceptional organizational skills, attention to detail, and ability to manage multiple priorities and deadlines effectively.

Professional Judgment & Confidentiality

Exercises discretion, professionalism, and sound judgment while handling sensitive and confidential information.

Communication

Communicates clearly, professionally, and effectively with internal and external stakeholders across all levels of the organization.

Collaboration

Builds positive and productive relationships across departments and supports a collaborative organizational culture.

Problem-Solving

Anticipates needs, identifies challenges, and develops practical and proactive solutions to support organizational goals.

Operational Mindset

Demonstrates strong understanding of organizational systems, workflows, compliance expectations, and operational efficiency.

Qualifications

Required

Bachelor’s degree in Business Administration, Human Resources, Education, Public Administration, or a related field; candidates with an Associate’s degree, project management certification, and relevant executive support experience may be considered

Minimum of one year of experience providing executive-level administrative or operational support

Strong organizational, communication, project management, and problem-solving skills

Ability to manage sensitive and confidential information with professionalism and discretion

Demonstrated ability to manage multiple priorities in a fast-paced virtual environment

Proficiency with Microsoft Office Suite, Google Workspace, and web-based systems

Must meet all PDE clearance requirements for school-based employees

Preferred

Experience in a public, charter, or cyber school environment

Knowledge of Pennsylvania Department of Education (PDE) requirements and reporting processes

Experience supporting executive leaders within a K–12 or virtual educational setting

Familiarity with state reporting systems such as PIMS

Experience developing SOPs, operational workflows, or project management systems

Physical & Work Environment Requirements

This is a remote position with occasional travel within Pennsylvania as needed.

Prolonged periods of sitting and computer use are required.

Ability to operate standard office equipment and computer systems.

Ability to occasionally lift and move items up to 25 pounds.