Executive Assistant; HR​/Legal

About Us

At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence.

HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions.

The Executive Assistant provides high-level administrative and operational support to the Chief Human Resources Officer (CHRO), the HR Leadership Team, and the Legal Leadership Team. This role serves as a critical operational hub, managing complex calendars, sensitive information, and coordination across two strategically vital functions. The ideal candidate is proactive and thrives in a fast-paced environment where priorities shift quickly and confidentiality is critical.

• Own a complex, dynamic calendar including executive team and Board meetings, recurring meetings (HR, HR Leadership Team, direct reports, Presidents, and Executive Management Team members), and other internal and external meetings. Independently decides what is scheduled and when based on priorities.
• Coordinate domestic and international travel arrangements, including detailed itineraries and navigating travel challenges.
• Submit expense reports in accordance with company policy.
• Prepare briefing materials, presentations, reports, and correspondence on behalf of and for the CHRO.
• Prioritize meeting requests and ensure timely CHRO follow-through on action items.
• Serve as a gatekeeper and trusted liaison between the CHRO and internal/external stakeholders.
• Submit invoices for payment and track expenses to ensure adherence to budget.

• Partner with the Lead Legal Executive Assistant for direction and coordination of Legal team support.
• Coordinate scheduling and logistics for HR and Legal leadership team meetings, offsites, training programs, and planning sessions.
• Plan and execute internal events for Legal and HR teams including annual functional summits and oversee all aspects including operations, logistics, vendor coordination, and event production.
• Coordinate employee engagement event planning in Chicago.
• Support onboarding of new HR and Legal leaders.
• Support onboarding of new Executive Assistants.
• Partner with HR and Legal team members on special projects and ongoing administrative tasks.
• Support project planning and management.

• 5+ years of executive assistant or senior administrative experience, with at least 2 years supporting C-suite executives.
• Demonstrated ability to manage competing priorities and operate effectively under pressure with minimal supervision.
• Strong attention to detail.
• Exceptional written and verbal communication skills; ability to draft executive-quality documents and communications.
• Advanced proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint) and collaboration tools (Teams, Zoom, SharePoint).
• Proven track record of maintaining strict confidentiality in a legal, HR, or executive environment.
• Strong project management skills with high attention to detail and follow-through.
• Proven success in driving for results and collaborating with others to make it happen.
• Adaptability and flexibility to adjust to changing business and leader needs.

• Experience supporting HR or Legal functions in a large company.
• Bachelor’s degree in Business Administration, Human Resources, Communications, or a related field.
• Experience supporting multi-functional or matrix leadership teams.
• Interest in a potential career in HR.