C-Suite Executive Assistant | Calendar & Travel Pro

Career Group; Chicago (IL); Hybrid; USD 80,000 - 110,000; Full time

Job summary

Career Group is seeking an exceptional Executive Assistant in the Chicago area to serve as a trusted right hand to a member of the C-suite. This high-visibility role goes beyond traditional administrative support, partnering closely with senior leadership to streamline priorities and keep a demanding schedule running smoothly.

The ideal candidate is sharp, proactive, and highly organized with excellent judgment and polished communication.

Qualifications

• 7+ years of Executive Assistant experience, ideally supporting C-suite or senior-level executives.
• Ability to manage highly complex calendars and domestic/international travel.
• Excellent written and verbal communication skills with the ability to interact confidently across all levels of an organization.
• Proactive and anticipatory, with a natural ability to identify needs before they are voiced.
• Strong organizational and project management skills with exceptional attention to detail.
• Excellent judgment, discretion, and ability to operate independently.
• Comfortable working a hybrid schedule in the Chicago area.

Responsibilities

• Manage a complex, ever-changing executive calendar, proactively balancing priorities and anticipating potential conflicts.
• Coordinate detailed domestic and international travel, including comprehensive itineraries, logistics, and contingency planning.
• Serve as a key liaison between the executive and board members, senior leadership, clients, and external partners.
• Draft, edit, and manage executive correspondence, board materials, presentations, and internal communications.
• Stay ahead of deadlines, meetings, and shifting priorities, ensuring the executive is prepared and informed.
• Coordinate logistics for board meetings, leadership meetings, offsites, and executive-level events.
• Manage special projects and drive follow-up on key action items on the executive’s behalf.
• Prepare and reconcile expense reports and assist with budget tracking and vendor coordination.
• Handle highly confidential business and personal matters with discretion and sound judgment.
• Provide occasional personal support as needed.

Skills

Calendar management

Travel coordination

Communication

Organizational skills

Discretion

Microsoft Office

Tools

Outlook

PowerPoint

Excel

Job description

Career Group is seeking an exceptional Executive Assistant in the Chicago area to serve as a trusted right hand to a member of the C-suite. This high-visibility role goes beyond traditional administrative support, partnering closely with senior leadership to streamline priorities and keep a demanding schedule running smoothly.

The ideal candidate is sharp, proactive, and highly organized with excellent judgment and polished communication.