Executive Assistant

Job Description

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.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to View email address on click.appcast.io learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy:

Skills and Requirements

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. Experience supporting a family office, family-owned company, ownership group, founder, or ultra-high-net-worth individual.

Experience balancing business support with appropriate personal, family, travel, or lifestyle-related logistics.

Experience directly supporting a President, EVP, senior operating executive, or member of an ownership group.

Experience within a large privately held company or complex enterprise organization.

Exposure to private aviation coordination.

Experience supporting an executive with significant customer, commercial, and external stakeholder responsibilities.

Experience coordinating across multiple Executive Assistants, offices, business units, household contacts, or family-office representatives.

Background in a high-touch hospitality, luxury service, concierge, or private-client environment combined with senior executive support experience.