Executive Assistant

Work Schedule

• 100% onsite, Monday–Friday

• This position is eligible for medical, dental, vision, and 401(k).

Our client is a growing software and technology organization in Chicago. The company offers an entrepreneurial, fast-moving workplace with a highly casual and technology-forward culture.

Our client is seeking an experienced Executive Assistant to provide high-level professional and personal support to a senior executive.

This is not a traditional administrative support position. The successful candidate will act as a true right hand, balancing executive support, personal assistance, travel logistics, scheduling, expenses, special projects, and lifestyle-related responsibilities.

The ideal candidate is exceptionally resourceful and comfortable receiving a goal or request without needing detailed instructions on how to accomplish it. This person should naturally research solutions, evaluate options, leverage technology and AI tools, make recommendations, and move tasks forward.

• Provide comprehensive executive and personal support while balancing multiple priorities in a fast-paced environment.
• Coordinate calendars, appointments, meetings, reservations, deliveries, and other professional or personal commitments.
• Handle lifestyle and household-related requests, including working with vendors, service providers, deliveries, and other personal logistics.
• Arrange complex domestic and international travel, including airfare, accommodations, transportation, reservations, and detailed itineraries.
• Track travel plans in real time and quickly develop alternative arrangements when schedules change.
• Anticipate upcoming needs, identify potential issues, and address them before they become problems.
• Manage expense reports, receipts, reimbursements, and supporting documentation.
• Coordinate with internal executive support professionals and senior leadership as needed.
• Conduct research and execute special projects with minimal direction.
• Assist with executive dinners, events, VIP experiences, and other high-touch arrangements.
• Serve as a responsive and professional point of contact for internal employees, external vendors, and personal contacts.
• Utilize AI and technology tools to research information, streamline tasks, draft communications, organize logistics, and improve efficiency.
• Maintain complete confidentiality when handling sensitive business and personal information.

• 3–5+ years of experience in executive support, personal assistance, lifestyle management, or another high-trust support position.
• Previous experience supporting a founder, senior executive, high-profile individual, or high-net-worth principal is strongly preferred.
• Demonstrated ability to work independently without requiring significant direction or oversight.
• Exceptional organizational skills with the ability to manage a large volume of competing priorities.
• Strong judgment and the confidence to make decisions when immediate direction is unavailable.
• Excellent written and verbal communication skills.
• Strong domestic and international travel coordination experience.
• Experience with expense management platforms such as Concur or Expensify.
• Proficiency with Microsoft Office and/or Google Workspace.
• Comfortable using AI tools such as ChatGPT, Claude, or similar platforms to research, plan, communicate, and problem-solve.
• High level of discretion and professionalism when working with confidential information.
• Ability to remain composed and solution-oriented when priorities or plans change unexpectedly.
• Strong sense of urgency, accountability, and attention to detail.
• Comfortable receiving direct feedback and working in a high-expectation environment.
• Significant exposure to senior…