Temporary Executive/Personal Assistant

Our client, a software development firm, is looking for a Temporary Executive/Personal Assistant. The ideal candidate will be professional, tech savvy, and have demonstrated ability to maintain strict confidentiality.

This position starts asap and will be an ongoing assignment with potential for permanent hire if the right fit.

Location: Chicago, IL

Hours: Monday – Friday from 8am – 5pm (24/7 mentality, some weekend work required as needed)

*Fully Onsite

Responsibilities:

• Provide day-to-day executive and personal support to the CEO as directed by the Sr. Director, Executive Operations
• Manage appointments, reservations, deliveries, household services, and personal logistics
• Serve as a responsive point of contact during assigned shifts, including occasional evenings and weekends
• Anticipate needs, proactively solve problems, and coordinate with vendors, service providers, and internal teams
• Coordinate complex domestic and international travel, including flights, hotels, ground transportation, itineraries, and contingencies
• Monitor travel in real time and quickly adjust plans as needed
• Support calendar management, prioritize scheduling requests, resolve conflicts, and ensure the CEO is prepared for all commitments
• Coordinate with Executive Assistants across the leadership team to align schedules and travel
• Manage receipts, expense reports, and reimbursements using Concur and Expensify
• Support special projects, research, events, dinners, VIP experiences, and personal errands
• Assist with process improvements within the Office of the CEO

Qualifications:

• 3–5+ years of experience in executive support/personal assistance
• Experience supporting a high-profile executive, founder, UHNW principal, or similarly demanding individual strongly preferred
• Exceptional organizational skills with the ability to manage multiple priorities in a fast-paced environment
• Excellent written and verbal communication skills with a polished, professional approach
• Proficiency with Concur, Expensify, travel booking platforms, Microsoft Office, and/or Google Workspace
• Strong AI fluency and demonstrated experience using tools such as ChatGPT and Claude to conduct research, plan logistics, draft communications, and streamline workflows
• Resourceful, proactive problem-solver with a strong sense of ownership and a service-oriented mindset
• Ability to maintain absolute discretion and confidentiality in all aspects of the role

Please submit your resume in Word format for immediate consideration.

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