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Job Description:

Job Title: Executive Assistant to the Chancellor’s Office

Department: The Chancellor’s Office

Job Purpose:

The Community Solution Education System is seeking an experienced Executive Assistant to provide direct support to the Chief of Staff and to work in close partnership with the Director of the Chancellor’s Office to support the effective functioning of the Chancellor’s Office as a whole. The Executive Assistant works in tandem with the Director of the Chancellor’s Office—aligning on responsibilities and coordinating efforts across projects, special events management, meeting preparation, Board Affairs support, and day-to-day operations—to ensure seamless support for the Chancellor and Chief of Staff. This role also provides administrative and coordination support to the Board Affairs Manager in support of system-wide Board affairs. The position has a direct reporting line to the Chief of Staff and a dotted-line relationship to the Director of the Chancellor’s Office, enabling strong collaboration, clear alignment of functions, and coordinated support across the office.

This position requires a strong in-office presence to coordinate activities, interface with other departments, and manage meeting logistics.

Position Overview

The Executive Assistant will deliver high-level, proactive administrative support to the Chief of Staff and the Chancellor’s Office team. This includes managing calendars, coordinating travel, processing expense reports and invoices, supporting strategic projects, and assisting with governance activities. The ideal candidate is highly organized, detail-oriented, and comfortable working in a fast-paced environment with senior executives and board members.

Position responsibilities include, but are not limited to:

+ Calendar & Scheduling: Manage complex calendars for the Chancellor and Chief of Staff; schedule meetings, appointments, and ensure all materials are prepared and distributed.

+ Travel Coordination: Arrange and confirm executive travel, ensuring a seamless experience.

+ Expense Management: Submit, reconcile, and track expense reports and departmental invoices.

+ Document Preparation: Draft, edit, and proofread documents including agendas, reports, correspondence, and presentations.

+ Meeting Support & Office Coordination:

+ Prepare daily calendars and meeting packets (PDF and printed) for in-office and remote days; ensure agendas and materials are attached to calendar entries.

+ Coordinate meeting set-ups, including room reservations, technology needs, catering, and on-site logistics.

+ Record and prepare accurate meeting minutes for key meetings, including Board-related sessions, and distribute promptly to appropriate stakeholders.

+ Assist the Director of the Chancellor’s Office on key projects and special events.

+ Board Affairs Support: Assist with preparation of materials, projects, and logistics related to Board of Trustees and governance activities.

+ Departmental Interface: Serve as a liaison between the Chancellor’s Office and other departments to ensure smooth communication and collaboration.

+ Communication: Monitor, scan, and categorize emails for the Chief of Staff; take action as appropriate; and flag urgent matters as needed.

+ Technology & Process Improvement: Learn and adapt to new tools to enhance team efficiency; identify opportunities to streamline processes.

Required Qualifications:

Knowledge and Skills

+ Proven experience supporting senior executives in a fast-paced environment.

+ Strong organizational and time-management skills with attention to detail.

+ Excellent written and verbal communication skills, including experience drafting meeting minutes.

+ Proficiency in Microsoft Office Suite and ability to learn new technology quickly.

+ Ability to handle confidential information with discretion.

+ Comfortable working in-office and coordinating across multiple departments.

+ High level of reliability, discernment, and commitment to maintain confidentiality.

+ High attention to detail is a must.

+ Must be responsive, quick-thinking, collaborative, demonstrate a willingness to learn, and possess an innate ability to anticipate and respond to issues.

+ Must be able to adapt to a fast-paced and changing environment while maintaining a positive attitude.

+ Must possess advanced knowledge/skills in Microsoft Office including Word, Excel, PowerPoint, OneDrive, Office 365 Suite, and Microsoft Outlook, understanding automation tools and advanced technology a plus.

+ Understanding of various programs such as, Microsoft Teams, Zoom, Diligent Boards, Concur, Workday. Must be willing to learn these applications.

+ Excellent written communication skills with consistent application of correct spelling, punctuation, and grammar for preparing and proofreading various documents and reports, including drafting and editing executive facing deliverables.

+ Ability to multi-task and maintain a high level of productivity and efficiency.

+ Ability to manage immediate requests and regular job duties with a sense of urgency.

Education:

+ Bachelor's degree, will consider experience in lieu of degree.

Experience:

+ Five+ years of related experience required.

Preferred Qualifications:

+ Preferred experience supporting advanced systems and experience with technology.

Working Conditions:

+ Willingness and flexibility to work outside regular business hours and the ability to travel, must be able to commute to Chicago System Office 5 days a week.

Compensation & Benefits

This opportunity is budgeted at $85,000 - 90,000 base compensation. Additional compensation factors may impact total compensation. To learn more about our competitive benefits and additional rewards, including generous paid time-off, medical and dental insurance coverage, life and disability insurance, retirement plan with employer contribution, multiple flexible spending accounts, tuition reimbursement, click the link below.

https://www.tcsedsystem.edu/careers/

The Community Solution is an Equal Opportunity Employer.

Application Process

Please note the screening, recruitment, and selection process is managed by recruiting staff and hiring managers with the aid of artificial intelligence to evaluate candidates against job requirements. The artificial intelligence tool is a resource only and all employment decisions are made by staff members.

When you apply, it is recommended you utilize the option to parse your resume into the application. To ensure your experience is accurately reflected, please review and complete all application fields—even if you auto-fill from your resume.

For the best results, tailor your resume to the job description, highlight key qualifications and skills, and use clear, consistent formatting. This helps our AI tools read and assess your application more effectively. We are committed to regularly monitoring the process for fairness and remove personally identifiable information during evaluation.