Executive Operations Assistant Jobs in Chicago, IL

Chicago Collegiate Charter School Network seeks a highly organized, proactive, and analytical Executive Operations Coordinator to serve as a key operational partner to the CEO and Network Leadership Team.

This role is responsible for creating organizational clarity, managing critical operational systems, coordinating executive workflows, and developing reporting structures that support decision-making across the organization.

The ideal candidate is a systems builder who thrives in fast-paced environments, enjoys bringing order to complexity, and can manage multiple priorities with professionalism and sound judgment. This individual will serve as a central coordinator across executive operations, budget workflows, reporting systems, network events, and stakeholder communications.

This is not a traditional administrative support role. The successful candidate will own key organizational processes and play a key role in improving the effectiveness of network leadership. 

Responsibilities include, but are not limited to: 

Executive Operations & Leadership Support

• Manage and optimize the CEO's calendar, meeting preparation, scheduling priorities, and follow-up systems
• Draft first versions of memos, communications, presentations, and executive correspondence
• Coordinate follow-up communications with donors, community partners, board members, and other stakeholders
• Maintain leadership action-item trackers and ensure timely completion of commitments
• Support meeting preparation through agenda development, document organization, and follow-up tracking

Organizational Systems & Process Management

• Serve as the primary coordinator for network-wide operational workflows
• Manage budget request intake and approval processes across schools and departments
• Review submissions for completeness and alignment with approved budgets prior to leadership review
• Develop and maintain systems that improve efficiency, accountability, and transparency
• Create documentation, standard operating procedures, and organizational resources

Initial Major Project

Lead the redesign and implementation of the network's Google Drive architecture, including:

• Folder structure redesign
• File naming conventions
• Document retention and archival protocols
• Access and permission management
• Security and privacy compliance alignment
• User training and implementation support

Data Reporting & Dashboard Development

• Develop and maintain executive dashboards that consolidate information from multiple data sources
• Produce weekly, monthly, and quarterly KPI reports for network leadership
• Track and report trends across:
  • Academic performance
  • Enrollment
  • Attendance
  • Finance and budget performance
  • Operational metrics
• Build reporting structures that transform existing data into actionable executive summaries
• Identify and highlight noteworthy trends, anomalies, or changes requiring leadership attention

Note: This role is responsible for reporting and trend identification, not instructional or strategic analysis.

Network Events & Professional Development Support

• Coordinate logistics for monthly network professional development sessions
• Prepare presentation templates and materials
• Manage event registration, communications, technology setup, and logistics
• Support execution of network meetings, retreats, and special events
• Ensure a high-quality participant experience

Community & External Relations Support

• Support community engagement and stakeholder outreach initiatives
• Assist with coordination of community meetings, events, and advocacy efforts
• Maintain stakeholder communication and follow-up systems
• Provide logistical support during legislative, community, and public engagement efforts

QUALIFICATIONS

Required

• Bachelor's degree or equivalent professional experience
• 3+ years of experience in operations, executive support, project coordination, program management, or a related field
• Advanced proficiency with Google Workspace
• Advanced spreadsheet skills (Google Sheets and/or Excel)
• Strong written communication skills
• Demonstrated ability to manage multiple projects simultaneously

Preferred

• Experience building dashboards or reporting systems
• Experience working in education, nonprofit, government, consulting, or mission-driven organizations
• Experience with Airtable, Looker Studio, Tableau, Power BI, or similar reporting platforms
• Experience coordinating complex projects involving multiple stakeholders

Desired Characteristics

The strongest candidates will demonstrate:

• Exceptional organizational skills
• Strong systems-thinking abilities
• High ownership and accountability
• Sound judgment and discretion
• Attention to detail
• Professional presence
• Comfort navigating ambiguity
• Ability to balance strategic projects with day-to-day execution
• Strong problem-solving skills
• Commitment to continuous improvement

Success in This Role

After one year, a successful Executive Operations Coordinator will have:

• Established reliable executive support systems for network leadership
• Implemented a modern, organized, and secure document management structure
• Built executive dashboards that provide clear visibility into key organizational metrics
• Streamlined budget request and approval workflows
• Improved organizational efficiency through stronger systems and processes
• Increased leadership capacity by reducing operational friction and ensuring consistent follow-through

Compensation and benefits are competitive and commensurate with experience.