Executive Assistant

Executive Assistant Approximately 10 or more years of progressive executive assistant experience supporting presidents, C-suite executives, EVPs, ownership stakeholders, or comparably senior leaders. Demonstrated experience independently managing complex and dynamic executive calendars. Significant experience coordinating domestic and international executive travel. Proven ability to anticipate needs, identify potential issues, and take action without requiring detailed direction. Experience supporting a senior executive in a fast-paced environment requiring flexibility, responsiveness, and confidentiality. Exceptional organization, prioritization, follow-through, and attention to detail. Outstanding written and verbal communication skills. Strong professional presentation and the ability to communicate confidently with senior executives, customers, ownership stakeholders, and external partners. Excellent judgment and discretion when handling sensitive business and personal information. Advanced proficiency with Microsoft Outlook and the broader Microsoft Office suite. Ability to work onsite in Rosemont, Illinois, five days per week. Ability to provide reasonable evening or weekend responsiveness when urgent executive or travel needs arise. Manage a complex and frequently changing executive calendar across internal meetings, customer engagements, travel, events, and select personal commitments. Anticipate scheduling conflicts, preparation needs, travel challenges, and executive priorities before they become issues. Own domestic and international travel planning, including flights, ground transportation, accommodations, itineraries, and real-time adjustments. Monitor active travel plans and proactively secure alternatives when cancellations, delays, weather, or other disruptions arise. Coordinate meetings with senior executives, customers, business leaders, ownership stakeholders, family-office contacts, and external partners. Provide support across professional responsibilities and appropriate personal or family-related scheduling and logistics. Coordinate private aviation and related transportation or itinerary requirements when applicable. Organize logistics for leadership meetings, customer engagements, executive events, family events, and other high-touch activities. Maintain accurate calendars, itineraries, contact information, reminders, and executive preferences. Manage expense reports, reimbursements, invoices, and related administrative processes accurately and promptly. Serve as a trusted point of contact between the executive and internal and external stakeholders. Build strong working relationships with executive leadership, other Executive Assistants, business partners, and external contacts. Handle highly confidential business and personal information with discretion and sound judgment. Remain reasonably accessible outside standard business hours when urgent travel, scheduling, or executive needs arise. Continuously identify ways to improve the executive's schedule, travel, communication, and overall workflow. Insight Global