Executive Assistant Office Manager

Insight Global; Chicago (IL); On-site; USD 34,000 - 55,000; Part time

Job summary

Insight Global is seeking an experienced Office Manager/Executive Assistant to support the firm's principals and run day-to-day office operations in River North, Chicago. The role combines executive support with office management and may include project coordination as needs evolve.

The ideal candidate is highly organized, proactive, professional, and able to work independently in a fast-paced environment with minimal training. 5–10+ years of related experience is preferred.

Qualifications

• 5-10+ years in office management or executive support roles.
• Experience supporting senior executives and managing calendars.
• Strong organizational and time-management skills.
• Excellent verbal and written communication with external stakeholders.
• Proficient with MS Office (Outlook, Teams, Word, Excel).
• Ability to work independently in a fast-paced, small-company environment.
• Discretion and confidentiality when handling sensitive information.

Responsibilities

• Provide high-level administrative support to principals and executives.
• Manage complex calendars, scheduling, and meeting coordination.
• Help executives stay organized, prepared for meetings and commitments.
• Coordinate travel, appointments, and scheduling needs.
• Serve as the primary contact for office operations and visitors.
• Greet guests, investors, attorneys, vendors, and other stakeholders.
• Manage mail, shipments, deliveries, and office supplies.
• Support employees with administrative needs.
• Coordinate with IT vendors to resolve office-related issues.
• Identify opportunities to improve office processes and efficiency.

Skills

Office management

Executive support

Calendar management

Travel coordination

Communication

Discretion

Microsoft Office

Tools

Microsoft Office Suite

Job description

Schedule: Onsite | Monday - Friday | 8:30 AM - 5:30 PM

Employment Type: 3-4 Contract (with potential for long-term consideration)

About the Company

Our client is a privately held real estate owner, investor, and developer based in the Chicago area. With a collaborative team of approximately 12 employees, they specialize in acquiring, developing, and managing real estate assets. They are seeking an experienced Office Manager / Executive Assistant to provide immediate support in their River North office.

Position Overview

This individual will serve as a key administrative partner to the firm's principals while also managing the day-to-day operations of the office. The ideal candidate is highly organized, proactive, professional, and able to work independently in a fast-paced environment with minimal training.

This role combines executive support responsibilities with office management duties and may expand to include project coordination support as business needs evolve.

Key Responsibilities

• Provide high-level administrative support to company principals and executives.
• Manage complex calendars, scheduling, and meeting coordination.
• Help executives stay organized, on track, and prepared for meetings and commitments.
• Coordinate travel, appointments, and other scheduling needs as required.
• Maintain professionalism and discretion when handling sensitive information.

Office Management

• Serve as the primary point of contact for office operations and visitors.
• Greet and assist guests, investors, attorneys, vendors, and other external stakeholders.
• Manage incoming and outgoing mail, FedEx shipments, messenger services, and deliveries.
• Order and maintain office, kitchen, and workplace supplies.
• Support employees with general administrative and operational needs.
• Coordinate with external IT vendors and service providers to resolve office-related issues.
• Ensure the office environment remains organized, professional, and fully operational.

Additional Support

• Assist with special projects and administrative initiatives as needed.
• Provide coordination support for internal projects and business operations.
• Identify opportunities to improve office processes and efficiency.

Qualifications

• 5-10+ years of office management, executive assistant, administrative support, or related experience.
• Experience supporting senior executives and managing complex calendars preferred.
• Strong organizational, multitasking, and time management skills.
• Excellent verbal and written communication skills with the ability to interact professionally with executives, investors, attorneys, vendors, and other external stakeholders.
• Proficiency with Microsoft Office Suite, including Outlook, Teams, Word, and Excel.
• Ability to work independently, take initiative, and thrive with minimal supervision.
• Professional, polished, and service-oriented demeanor.
• Detail-oriented with strong problem-solving skills and the ability to anticipate needs before they arise.
• Comfortable working in a small-company environment where flexibility, adaptability, and a hands-on approach are valued.
• Experience coordinating office operations, vendors, supplies, and administrative processes.
• Experience in commercial real estate, property management, development, or a related industry is a plus, but not required.
• Comfortable learning new systems and technologies as needed.
• Proven ability to maintain discretion and confidentiality when handling sensitive information.