IWiL: Insurance Women in Leadership – West Point, NY 2026

Summary

The workforce and markets are shifting and agency & broker executives can rise to meet new challenges by understanding strengths, influencing talent to excel, and inspiring positive change within organizational structures.

IWiL participants will have the opportunity to partner with influential United States Military officers in a journey to define and refine their leadership styles and equip themselves to meet today’s ever changing business demands.

Participants will be introduced to leadership models that can produce more motivated, efficient, and satisfied team members. The program provides teams with tools to solve problems in which they are challenged to think creatively, act as high-performing units, and learn from failures and successes.

Women will leave this program with an enhanced understanding of and a pathway towards leading with vision, purpose, and positive impact.

PHASE 1 | VIRTUAL: Sept 14 – Oct 2 | Blend of synchronous and asynchronous virtual activities
PHASE 2 | IN PERSON: Oct 14 – 16 | Workshops and Experiential Activities at West Point
PHASE 3 | VIRTUAL: Oct 2026 – Feb 2027 | Two one-on-one coaching sessions

Please review the PHASES section below for additional details on program cadence & timing.

Register Now View Program Catalog Page

Program Outline

Phase 1 | Virtual

Sept 14 – Oct 2, 2026

Sept 14 Online self-paced (1 hour)
Sept 16 – 23, Online self-paced (CliftonStrengths 34 Assessment)
Sept 23, 1:00 – 2:00 PM ET Zoom, Live
Sept 25 – 30 Online self-paced (3 lessons)
Oct 2 Online self-paced (30 mins)

Phase 2 | In-Person

Oct 14 – Oct 16, 2026

Oct 14 12:00 PM ET Arrival
Oct 16 1:30 PM ET Departure

Phase 3 | Virtual

Oct 2026 – Feb 2027

Two one-on-one post program coaching sessions

Are you…

Faculty Spotlight

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Location & Lodging

This program includes overnight hotel accommodations for October 14 and 15. In order to guarantee hotel availability participants must register for the program by September 14. Hotel accommodation is not guaranteed for participants who register after the cut off date. Participants are responsible for their own travel expenses and for making their own travel arrangements to and from the United States Military Academy in West Point, NY.

The Historic Thayer Hotel on the grounds of the United States Military Academy at West Point, NY
674 Thayer Rd
West Point, NY 10996
website | map

Tuition

Cornerstone Rate: $3,000
Standard Rate: $6,000
Includes program fees, accommodations & meals.

Attire

Business casual for classroom sessions. Athletic wear for experiential sessions.

Chubb Contact

Kathleen Wooldridge
Chubb Agency Education Manager
koverlin@chubb.com
615-975-0429

About Thayer Leadership

Thayer Leadership is a premier executive leader development program, based on the grounds of the United States Military Academy (U.S.M.A.) at West Point, New York. Founded in 2010, Thayer Leadership has trained more than 50,000 executives and front-line leaders from over 250 companies across a variety of industries earning an average net promoter score of 93%. Utilizing a diverse range of customized, open enrollment, and online learning programs, Thayer Leadership’s mission is to help build leaders of character by offering leadership and ethics education grounded in the U.S. Army leadership philosophy of “Be, Know, Do” and the U.S.M.A. values of “Duty, Honor, Country”. Connect with them on LinkedIn, Facebook, and Twitter.

Cancellation Policy

A minimum 14 day notice is required to guarantee a full refund. Please send cancellation requests to agency_education@chubb.com. Include “Program Cancellation Request” in the subject line, and your original registration information in the message body along with the reason for the cancellation.

Registration

To register for the program, complete the form below and indicate your preferred payment method. 

If you select check payment, please mail your tuition check in the amount of $6,000 ($3,000 for Cornerstone agencies) and include a copy of your registration confirmation or indicate the participants name and “IWiL – Oct, 2026” on the check. Send checks payable to ‘ACE American Insurance Company’ to: 

Jessica Albert
Chubb Agency Education
202 Hall’s Mill Road
Building A – 2E
Whitehouse Station, NJ 08889-1600 

If you select credit card payment you will receive an invoice via email with payment instructions within 10 business days. Invoices will come from the email address ‘service@paypal.com’ with ‘Invoice from Federal Insurance Co’ in the subject line. You may wish to whitelist this email address or check your spam folders after 10 days have passed

Log in or create an account for faster registration and access to premium content.

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Registration for IWiL: Insurance Women in Leadership October 2026

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