Temporary Executive Assistant

City Staffing; Chicago (IL); Hybrid; USD 100,000 - 108,000; Full time

Job summary

City Staffing is seeking an experienced Executive Assistant to support the CEO in a long-term temporary, hybrid role in Downtown Chicago, IL. The position will require in-office presence on days when the CEO is in, with flexible remote work as needed.

Responsibilities include calendar management, travel coordination, correspondence preparation, and event support, plus light project management for leadership initiatives.

Qualifications

• Proven experience as an executive assistant, preferably supporting a CEO/founder.
• Bachelor’s degree preferred.
• Excellent organizational and time management skills.
• Strong written and verbal communication abilities.

Responsibilities

• Collaborate closely with the CEO, anticipating needs and delivering solutions.
• Manage complex calendars, schedule appointments, and coordinate meetings.
• Arrange travel itineraries and logistics for domestic and international trips.
• Assist with calendar management and travel for the executive team as needed.
• Prepare and edit correspondence, presentations, and other documents.
• Serve as point of contact with executives and internal/external stakeholders.
• Support event planning for company conferences and team meetings.
• Provide light personal assistance to the CEO as required.
• Support basic project management of leadership initiatives to keep deadlines.

Skills

Scheduling

Project management

Office tools

Communication

Time management

Organizational skills

Education

Bachelor’s degree

Tools

Microsoft Office

Google Workspace

Slack

Job description

This is a long term temporary, hybrid role located in Downtown Chicago, IL.

Duration: Long Term Temporary Contract expected to last from Mid October 2026 through Early April 2027

Schedule: Monday through Friday

please note that while this role can largely be performed from home, the Executive Assistant will be expected to be in the Downtown Chicago office on days when the CEO is in.

Pay Rate: $48-52 per hour

Our client, a Chicago based startup, is looking for a temporary Executive Assistant to assist with leave coverage.

• Collaborate closely with the CEO, anticipating needs and providing solutions that enhance their productivity and effectiveness.
• Manage complex calendars, scheduling appointments, and coordinating meetings, ensuring efficient use of the CEO's time with internal and external obligations.
• Arrange travel itineraries, accommodations, and logistics for domestic and occasional international trips.
• Assist with occasional calendar management and travel coordination for executive team as a whole to ensure attendance at mandatory events.
• Prepare and edit correspondence, communications, presentations, and other documents.
• Act as the point of contact between executives and internal/external stakeholders, maintaining professionalism and confidentiality.
• Assist in organizing company events, conferences, and team meetings.
• Assist with the basic project management of executive leadership initiatives, ensuring projects remain on track and deadlines are met.
• Provide light personal assistance to the CEO, including managing personal appointments, household arrangements, and private events.
• Proven experience as an executive assistant, preference for experience with CEO/Founders.
• Excellent organizational and time management skills, with the ability to prioritize tasks and anticipate needs.
• Strong communication skills (written and verbal), with the ability to interact effectively with executives, staff, and external contacts.
• Proficiency in scheduling, project management, and office productivity tools such as Microsoft Office, Google Workspace, and Slack.
• Ability to prioritize, multi-task, and adapt to the constantly changing needs of a busy CEO.
• Bachelor’s degree preferred; relevant certifications or additional coursework a plus.

City Staffing is committed to diversity, equity, and inclusion (DEI) in all aspects of our business. As a women-owned and operated business, WBE certified, we recognize the importance of creating an inclusive and welcoming work environment for all individuals regardless of age, race, creed, color, national origin, sex, ability, marital status, gender identity and/or expression, or sexual orientation.