Executive Assistant Trainer (Part-Time) at City Staffing

This is a fully onsite position in Chicago, IL.

Schedule

Part-Time | 2 days per week, with flexibility on days

Location

onsite in Downtown Chicago

Duration: 3 months with potential for extension

Comp: $35 - 40/hour

Our client, a Chicago-based investment firm, seeks someone experienced in executive travel management to mentor and train an existing executive assistant.

Responsibilities:

• Work alongside the current Executive Assistant to coordinate upcoming domestic and international travel arrangements for executives, providing step-by-step guidance throughout the process.
• Establish and document Standard Operating Procedures (SOPs), templates, and checklists to create repeatable, scalable workflows for travel coordination.
• Introduce effective tools, resources, and industry best practices, ensuring the Executive Assistant is equipped with the necessary skills to independently manage travel logistics in the future.
• Share insights and "tricks of the trade" to navigate potential challenges, last-minute changes, and travel disruptions efficiently.
• Assess and recommend software, services, and tools that enhance productivity and streamline travel planning.
• Allocate some remote hours for pre-planning training materials and resources prior to onsite sessions.

Qualifications:

• Minimum 5 years of experience as an Executive Assistant, Travel Coordinator, or similar role supporting senior executives, including extensive domestic and international travel planning.
• Demonstrated ability to train and mentor others, particularly in specialized administrative functions.
• Proficiency with travel management platforms, itinerary planning tools, and expense tracking systems.
• Proven skill in troubleshooting travel-related issues and creating contingency plans.
• Exceptional organizational skills and attention to detail in managing schedules, itineraries, and documents.
• Clear and professional communication style, with the ability to explain processes effectively.
• Ability to adapt to evolving schedules and priorities with professionalism and a positive attitude.

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.

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