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IWiL: Insurance Women in Leadership – West Point, NY

October 9 - October 11

United States Military Academy – Historic Thayer Hotel


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 9 – Oct 2 | Blend of synchronous and asynchronous virtual activities
PHASE 2 | IN PERSON: Oct 9 – 11 | Workshops and Experiential Activities at West Point
PHASE 3 | VIRTUAL: Oct 2024 – Feb 2025 | Two one-on-one coaching sessions

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

Program Overview Video

Program Outline

  • Principles of Strengths Based Leadership
  • Leadership Resilience Practice
  • West Point Leadership Overview through a Historical Guided Experience
  • Team Training & Experiential Learning Activities
  • Commander’s Call and Action Planning

Phase 1 | Virtual

Sept 9 – Oct 2, 2024

Sept 9 Online self-paced
(1 hour)
Sept 18, 1:00 – 2:00 PM ET Zoom, Live
Sept 20 – 25 Online self-paced (3 lessons)
Sept 30, 1:00 – 2:00 PM ET Zoom, Live
Oct 2 Online self-paced
(30 mins)

Phase 2 | In-Person

Oct 9 – Oct 11, 2024

Oct 9 12:00 PM ET Arrival
Oct 11 1:30 PM ET Departure

Phase 3 | Virtual

Oct 2024 – Feb 2025

Two one-on-one post program coaching sessions

Are you…

  • A female leader within your organization?
  • Ready to take your business to the next level?
  • Committed to your own personal development?


  • Understand how values impact leadership success and how to inspire and motivate my team to their fullest potential
  • Apply principles of strength based leadership that will allow me to lead my business to outstanding results, lead organizational change, and create an environment that inspires and focuses on desired outcomes
  • Obtain leadership thinking ability and skills for my current and future roles
  • Build self-awareness and understand my impact on others
  • Develop leadership resilience to cope with setbacks with a positive mindset
  • Learn how to cope positively in the face of challenges, bounce back from adversity, and thrive
  • Gain knowledge of the tools that can better prepare me to adapt to the uncertainties of a changing world and workplace
  • Examine strategies for using my strengths to increase my personal well-being

Faculty Spotlight

Brigadier General (Retired)
Becky Halstead, USMA 1981
Program Senior Advisor

First Female Graduate of West Point to be promoted to General Officer. Learn more about Becky’s experience.


Kimberly Jung, US Army
Keynote Speaker

US Army Engineer Officer, Co-Founder Rumi Spice, ABC’s Shark Tank Winner, IWA Women Extraordinaire Award Recipient, Tillman Foundation’s Make your Mark Award Recipient. Learn more about Kimberly’s experience.

Location & Lodging

This program includes overnight hotel accommodations for October 9 and 10. In order to guarantee hotel availability participants must register for the program by September 17th. 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


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


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

Chubb Contact

Kathleen Wooldridge
Chubb Agency Education Manager

About Thayer Leadership

Thayer LeadershipThayer 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 LinkedInFacebook, 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.


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, 2024” 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.

IWiL: Insurance Women in Leadership 2024 1009 1011

Your Information

Registration for IWiL: Insurance Women in Leadership 2024 10/09-10/11
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October 9
October 11
Event Categories:
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United States Military Academy – Historic Thayer Hotel
674 Thayer Rd.
West Point, NY 10996 United States
+ Google Map


Kathleen Wooldridge