Jonathan Littlefield

Jonathan Littlefield's work experience includes various roles at different companies. Jonathan started their career as a Loss Control Engineer at Verlan Fire Insurance Company in 1999 and worked there until 2000. Jonathan then joined Digex as a Product Planning Intern from 2001 to 2002.

In 2002, Jonathan joined The Hanover Insurance Group, where they held multiple positions. Jonathan began as the Director of Business Planning for Hanover Specialty Industrial Property and worked in this role until 2008. Jonathan then became the Director of Distribution Management for Hanover Specialty Industrial until 2012. From 2012 to 2021, they served as the AVP of Hanover Specialty Insurance Brokers (HSIB).

Since 2021, Jonathan has been working at W. R. Berkley Corporation. Jonathan started as the AVP of Small Commercial and Select Accounts for Berkley Aspire and held this role until 2023. Currently, they are the VP of Strategy, Operations, and Innovation for Berkley Aspire.

Jonathan Littlefield earned a Bachelor of Science degree in Fire Protection Engineering from the University of Maryland - James A Clark School of Engineering in 1997. Jonathan then pursued a Master of Business Administration degree at the University of Maryland - Robert H. Smith School of Business from 2000 to 2002.