Executive Administrative Assistant, TII

Travel Insured International,a Crum & Forster company, is hiring an Executive Administrative Assistant.

Travel Insured International is a leading travel insurance provider with more than 30 years in business. As a key component of our Specialty Business Unit (SBU), within the Accident & Health division, TII provides travel protection plans to help each individual travel confidently. Travel Insured International is proud to offer products to consumers and to agency partners of all sizes. We are committed to providing dependable coverage, great value, and end-to-end satisfaction for all customers.

The Executive Administrative Assistant (EA) serves as a trusted partner to the President, TII and to other senior executive leaders, anticipating needs, identifying risks and opportunities in advance, and exercising sound judgment in a fast-paced, growth-oriented environment.

This EA will manage a broad range of responsibilities supporting both strategic and administrative needs.

The EA will help ensure meetings and materials are efficient and effective and will facilitate the flow of critical business information across TII.

The ideal candidate will bring strong planning, prioritization, and time management skills, orchestrating complex calendars and scheduling operations running smoothly and efficiently. This role requires seamless interaction with senior executive management within TII and the A&H division, department leaders, and employees across TII.

This is a hybrid position (2 days per week; days of the office are flexible) located at our Glastonbury, Connecticut office.

What you will do:

• Proactively coordinate and own the calendar of the President, TII, including internal and external meetings, conferences, seminars and travel industry events.
• Partner with the President to shape priorities and sequence the week; synthesize information, prepare briefings, and surface emerging issues, risks, and opportunities before they escalated.
• Evaluate meeting requests and prioritize executive time in alignment with business objectives; balance competing demands across multiple leaders, anticipate scheduling conflicts, and recommend solutions in advance.
• Coordinate domestic and international travel end-to-end, including itineraries, ground transportation, hotel and meeting logistics, time-zone planning, contingency plans, and preparation or recovery time.
• Prepare the President and other executives for meetings by assembling relevant background, materials, and agendas; document notes, identify action items, and drive follow-up to completion, tracking deliverables, timelines, and deadlines and escalating issues as appropriate.
• Draft, edit, and finalize correspondence, white papers, presentations, agendas, spreadsheets, dashboards and reports; prepare and distribute weekly email or One Note updates to relevant stakeholders
• Use generative AI and Microsoft Copilot to synthesize source materials, develop meeting briefs and executive summaries, draft and refine communications and presentations, organize information, and accelerate high-quality executive deliverables.
• Identify practical opportunities to use AI and automation to reduce manual effort, improve workflows and follow-through, and create additional capacity for the President and executive team.
• Apply sound judgment when using AI-generated content, including validating material information against source materials and maintaining appropriate confidentiality and data-handling practices.
• Prepare, submit in Concur and track the President’s expense reports, ensuring receipts, business purpose, coding, allocations, policy compliance and timely follow-up. Follow up on late expense report submissions for others.
• Coordinate…