Executive Assistant

Legends Hospitality LLC; United States; On-site; USD 70,000 - 100,000; Full time

Job summary

Legends Global is seeking an organized, proactive Executive Assistant & Office Manager to support executive leadership and oversee daily office operations in Chicago. The role requires confidentiality, sound judgement, and the ability to balance priorities in a fast-paced environment.

The candidate will manage complex calendars, coordinate travel, prepare reports, and ensure an efficient, welcoming office. Experience with C-level support and MS Office is essential.

Qualifications

• 5+ years of experience supporting senior executives in an EA/Office Manager role.
• Experience supporting C-suite or senior leadership preferred.
• Strong organizational, time management, and confidentiality skills.
• Excellent written and verbal communication; ability to work independently.

Responsibilities

• Provide dedicated administrative support to executive leadership, including calendar management, meeting coordination, and scheduling.
• Coordinate domestic and international travel arrangements, including itineraries, accommodations, and transportation.
• Prepare and process expense reports in a timely manner.
• Draft, edit, and format presentations, reports, meeting agendas, correspondence, and other business documents.
• Coordinate executive meetings, including room reservations, materials, catering, and follow-up action items.
• Serve as a trusted liaison between executives and internal and external stakeholders.
• Prioritize competing requests and proactively manage changing priorities.
• Handle confidential and sensitive information with professionalism and discretion.
• Support special projects and strategic initiatives as assigned.

Skills

Executive support

Office management

Calendar management

Travel coordination

Expense reporting

MS Office Suite

Tools

Expense reporting systems

Calendar management tools

Job description

Job Title: Executive Assistant

Location: Chicago, IL

Department: Administrative

FLSA Status: Exempt, Salaried

Legends Global is seeking a highly organized, proactive, and service-oriented Executive Assistant & Office Manager to support executive leadership while overseeing the daily operations of our Chicago office. This highly visible role serves as a trusted partner to senior leaders, ensuring seamless administrative support while creating an efficient, welcoming, and well-managed office environment. The ideal candidate thrives in a fast-paced environment, exercises sound judgment, maintains confidentiality, and can successfully balance executive priorities with office operations. This individual will be instrumental in helping our leadership team stay organized while fostering an exceptional workplace experience for employees and visitors.

ESSENTIAL DUTIES AND RESPONSIBILITIES

Executive Assistant Support

• Provide dedicated administrative support to executive leadership, including complex calendar management, meeting coordination, and scheduling.
• Coordinate domestic and international travel arrangements, including itineraries, accommodations, and transportation.
• Prepare and process expense reports in a timely manner.
• Draft, edit, and format presentations, reports, meeting agendas, correspondence, and other business documents.
• Coordinate executive meetings, including room reservations, materials, catering, and follow-up action items.
• Serve as a trusted liaison between executives and internal and external stakeholders.
• Prioritize competing requests and proactively manage changing priorities.
• Handle confidential and sensitive information with the highest level of professionalism and discretion.
• Support special projects and strategic initiatives as assigned.

Office Management

• Oversee the day-to-day operations of the Chicago office to ensure a professional, organized, and efficient workplace.
• Serve as the primary point of contact for office vendors, building management, and facilities-related needs.
• Manage office supplies, equipment, inventory, mail distribution, and common areas.
• Coordinate office maintenance requests and ensure workspaces remain functional and welcoming.
• Partner with HR and IT to coordinate onboarding logistics for new employees, including workspace setup, equipment, badges, and office orientation.
• Plan and coordinate office events, employee engagement activities, meetings, and team celebrations.
• Help maintain office policies, procedures, and operational best practices.
• Identify opportunities to improve office processes and employee experience.

Qualifications

• 5+ years of experience supporting senior executives as an Executive Assistant, Office Manager, or similar administrative role.
• Experience supporting C-level or senior executive leadership strongly preferred.
• Exceptional organizational and time management skills with the ability to manage multiple priorities simultaneously.
• Strong written and verbal communication skills.
• Demonstrated ability to exercise sound judgment, maintain confidentiality, and work independently.
• Highly proactive with strong problem-solving and decision-making abilities.
• Professional, polished demeanor with excellent interpersonal skills.
• Advanced proficiency with Microsoft Office Suite, including Outlook, Word, Excel, and PowerPoint.
• Experience with expense reporting systems and calendar management tools preferred.

COMPENSATION

Competitive salary, commensurate with experience, and a generous benefits package that includes medical, dental, vision, life and disability insurance, paid vacation, and 401k plan.

WORKING CONDITIONS

Location: Chicago, IL

PHYSICAL DEMANDS The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

NOTE: The essential responsibilities of this position are described under the above headings. They may be subject to change at any time due to reasonable accommodation or other reasons. Also, this document in no way states or implies that these are the only duties to be performed by the employee occupying this position.

Legends Global is an Equal Opportunity/Affirmative Action employer, and encourages Women, Minorities, Individuals with Disabilities, and protected Veterans to apply. VEVRAA Federal Contractor.

Our Work Experience is the combination of everything that's unique about us: our culture, our core values, our company meetings, our commitment to sustainability, our recognition programs, but most importantly, it's our people. Our employees are self-disciplined, hard working, curious, trustworthy, humble, and truthful. They make choices according to what is best for the team, they live for opportunities to collaborate and make a difference, and they make us the #1 Top Workplace in the area.