Executive Administrative Assistant, TII

Crum & Forster • Glastonbury, CT

6d • $53,400 - $89,000 • Hybrid

About The Position

Travel Insured International, a Crum & Forster company, is hiring an Executive Administrative Assistant to serve as a trusted partner to the President, TII, and other senior executive leaders. The role anticipates executive needs, identifies risks and opportunities, and exercises sound judgment in a fast-paced, growth-oriented environment. It supports strategic and administrative needs, helps make meetings and materials effective, and facilitates the flow of critical business information across TII.

The position manages complex calendars and scheduling, coordinates travel, prepares executives for meetings, supports follow-through on decisions and deliverables, and produces executive communications and materials. It also uses generative AI and Microsoft Copilot to improve executive work and workflows, while validating AI-generated information and maintaining appropriate confidentiality and data-handling practices. Additional work includes expense reporting, customer or partner escalations, event support, office and administrative operations, cross-functional liaison duties, and special projects.

This is a hybrid position based at the Glastonbury, Connecticut office, with two office days per week; the days are flexible.

Requirements

• High school diploma required.
• Six or more years of experience supporting a senior executive, preferably a C-level executive or equivalent leader in a fast-moving organization.
• Intermediate to advanced proficiency with Microsoft Outlook, Excel, Word, PowerPoint, Teams, and SharePoint.
• Demonstrated working proficiency with generative AI tools, with examples of using AI to improve productivity, synthesize information, develop or refine written materials, prepare presentations or meeting materials, or improve workflows.
• Ability to manage multiple priorities, shifting demands, and tight deadlines in a fast-paced environment.
• Excellent verbal and written communication skills.
• High attention to detail and accuracy.
• Proactive, self-directed, and adaptable to changing priorities.
• Ability to abide by departmental policies and procedures, including authority levels, to comply with C&F risk management controls.
• Ability to work a hybrid schedule, ideally two days in the office.

Nice To Haves

• Associate’s degree or equivalent work experience.
• Practical experience using Microsoft Copilot; candidates without direct Copilot experience should demonstrate meaningful experience with comparable generative AI tools and aptitude to become proficient with Copilot.
• Travel-industry or insurance-industry experience; experience in airlines, cruise, hospitality, tourism, or travel technology is also preferred.

Responsibilities

• Proactively coordinate and own the President, TII’s calendar, 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.
• Evaluate meeting requests and prioritize executive time according to business objectives; balance competing demands across leaders, anticipate scheduling conflicts, and recommend solutions.
• Coordinate domestic and international travel end-to-end, including itineraries, ground transportation, hotels, meeting logistics, time-zone planning, contingency plans, and preparation or recovery time.
• Prepare executives for meetings by assembling background materials and agendas; document notes, identify action items, track deliverables and deadlines, drive follow-up, and escalate issues as appropriate.
• Draft, edit, and finalize correspondence, white papers, presentations, agendas, spreadsheets, dashboards, and reports; prepare and distribute weekly email or OneNote updates to stakeholders.
• Use generative AI and Microsoft Copilot to synthesize source materials, create meeting briefs and executive summaries, draft and refine communications and presentations, organize information, and accelerate executive deliverables.
• Identify opportunities to use AI and automation to reduce manual effort, improve workflows and follow-through, and create capacity for the President and executive team.
• Validate material information in AI-generated content against source materials and maintain 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 reports for others.
• Coordinate presidential-level customer or partner escalations with urgency, empathy, and judgment.
• Partner with the Events & Sponsorships team as needed for internal and external functions.
• Greet and assist visitors in the Glastonbury office as needed.
• Support administrative operations such as NDA requests, document uploads to the contract management system, and program renewal tracking.
• Source office supplies and manage e-filing systems.
• Serve as a point of contact for general communications and as a liaison across TII teams and divisional Shared Services, including Compliance, Legal, Regulatory, and Finance.
• Take on designated special projects and support other leadership team members as needed.
• Perform other duties as assigned.

Benefits

• Competitive compensation package.
• Generous 401(k) employer match.
• Employee Stock Purchase Plan with employer matching.
• Generous paid time off.
• Benefits beyond health, dental, and vision focused on physical, mental, and financial wellbeing for employees and their families.
• Tuition reimbursement, industry-related certifications, and professional training.
• Matching donation program, volunteer opportunities, and an employee-driven corporate giving program.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: High school or GED