Executive Administrative Assistant, TII

Crum & Forster Company Overview

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.

Job Description

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 escalate.

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 presidential-level customer or partner escalations with urgency, empathy and judgment.

Partner with Events & Sponsorships team as needed for internal and external functions.

Greet and assist visitors in the Glastonbury office as needed.

Support administrative operational tasks such as NDA requests, uploading documents to contract management system, tracking program renewals, etc.

Source office supplies and manage e-filing systems.

Act as a point of contact for general communications and as a liaison across all teams/functions with TII and divisional Shared Services (Compliance, Legal, Regulatory, Finance, etc.,).

Take on special projects as designated, support other members of the leadership team as needed.

Perform other duties as assigned.

What YOU will bring to C&F:

Clear, concise executive-level writing that distills complex information into actionable summaries

Demonstration of confidence, discretion, diplomacy, and sound judgment when interacting with senior executives, leaders, partners and external stakeholders

Demonstrated proficiency using generative AI tools to improve productivity and the quality and speed of work, particularly for information synthesis, drafting, executive communications, meeting preparation and presentation development.

Strong curiosity and aptitude to continually advance use of Microsoft Copilot and other approved AI and automation capabilities to improve how the President and executive team work.

Ability to use AI thoughtfully and responsibly, recognizing when source validation, judgment and human review are required.

Highly proactive

Executes details reliably

Empathetic

Approachable

Requirements:

High school diploma required.

Associate’s degree or equivalent work experience preferred.

6+ years of experience supporting a senior executive, preferably a C-level executive or equivalent leader in a fast-moving organization.

Intermediate to Advanced proficiency in Microsoft Office tools – Outlook, Excel, Word, PowerPoint, Teams and SharePoint.

Demonstrated working proficiency with generative AI tools is required. Candidates should be able to provide examples of how they have used AI to improve productivity, synthesize information, develop or refine written materials, prepare presentations or meeting materials, or improve workflows.

Practical experience using Microsoft Copilot is strongly preferred. Candidates without direct Copilot experience must demonstrate meaningful experience with comparable generative AI tools and the aptitude to quickly become proficient with Copilot.

Ability to effectively 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.

Will abide by departmental policies and procedures, including authority levels, to comply with C&F's risk management controls.

Travel-industry or insurance industry experience is strongly preferred. Experience in airlines, cruise, hospitality, tourism, travel technology are also preferred.

Ability to work a hybrid schedule, ideally 2 days in the office.

What C&F will bring to you

What C&F will bring to YOU:

Competitive compensation package

Generous 401K employer match

Employee Stock Purchase plan with employer matching

Generous Paid Time Off

Excellent benefits that go beyond health, dental & vision. Our programs are focused on your whole family’s wellness including your physical, mental and financial wellbeing

A core C&F tenant is owning your career development so we provide a wealth of ways for you to keep learning, including tuition reimbursement, industry related certifications and professional training to keep you progressing on your chosen path

A dynamic, ambitious, fun and exciting work environment

We believe you do well by doing good and want to encourage a spirit of social and community responsibility, matching donation program, volunteer opportunities, and an employee driven corporate giving program that lets you participate and support your community

At C&F you will BELONG:

We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you require a special accommodation, please let us know.

For California Residents Only: Information collected and processed as part of your career profile and any job applications you choose to submit are subject to our privacy notices and policies, visit https://www.cfins.com/onlineprivacypolicy/ca/noticeatcollection/ for more information.

Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws. Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $53,400 to a maximum of $89,000. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee’s contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.

#LI

#MU