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Jeanne Fenster
Division President

Jeanne R. Fenster is the President of Berkley Prime Transportation and has nearly 25 years of experience in the property casualty insurance industry with a focus on personal auto and commercial auto lines of business. She holds a Juris Doctorate from Vanderbilt University School of Law and a Bachelor of Science in Mathematics and Psychology from the University of Memphis.

Kathleen Fleming, CPCU, AU
Assistant Vice President – Underwriting

Katie has worked in the insurance industry for close to 30 years, and with the Berkley organization for over 12 years. Over the course of her career, Katie has held numerous underwriting and technical positions, including most recently as the Underwriting Manager at Carolina Casualty, a Berkley company. Katie is currently serving as the Assistant Vice President of Underwriting for Berkley Prime Transportation.

Katie earned a Bachelor of Science in Business Administration from Bloomsburg University of Pennsylvania. She continued her insurance education by earning multiple designations through the Insurance Institutes including the Associate in Underwriting (AU) and Chartered Property Casualty Underwriter (CPCU).

May Miao, FCAS
Senior Product and R&D Analyst

May began her career with Berkley Prime Transportation in January of 2019 and is currently leading the analytical efforts as a Senior Product and R&D Analyst. Prior to joining Berkley Prime Transportation, May worked at W. R. Berkley Corporation headquarters in Greenwich, CT for five years as Actuarial/Predictive Modeling Analyst. May gained diverse modeling experience in collaboration with other Berkley companies across different lines of business in her previous roles. She holds a Master of Mathematics degree in Actuarial Science from University of Waterloo, and is a Fellow of the Casualty Actuarial Society (FCAS).

Cindy DeLeon, MBA
Operations Manager

Cindy DeLeon is the operations manager at Berkley Prime Transportation. She brings over sixteen years of insurance experience across key business functions including product development, straight through processing, telematics, vendor management, and project management.

Cindy earned a Bachelor’s Degree in Business Administration and a Master’s Degree in Business Administration with a minor in Accounting from Albertus Magnus College.

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