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James R. Bennett has an extensive work experience in the insurance industry. James R. worked as a Regional Vice President - Sales at Hudson Insurance Group starting in 2011. Prior to this, they were a Regional Marketing Manager at Diversified Crop Insurance Services from 2003 to 2010. James R. also served as a Regional Manager at American Agrisurance Inc. from 2002 to 2003, where they were responsible for training, recruiting, and marketing crop insurance agents. Before that, they worked as a Regional Vice President at IGF Insurance Company from 1996 to 2003, managing and training crop insurance agents in multiple states. James R.'sprevious roles include being a Field Supervisor at Farmers Mutual Hail Insurance Company of Iowa from 1994 to 1996 and an MPCI Adjuster at RCIS: Rural Community Insurance Services from 1990 to 1994. James R. started their career as a Crop Hail Adjuster at Farmers Mutual Hail Insurance in 1989. James R. Bennett also had experience as a farmer at Meadow Creek Farms from 1986 to 1994.

James R. Bennett holds a Bachelor of Science degree in Agri-Business from Illinois State University. Additionally, they have obtained the Illinois Property Casualty Producer License from the Illinois Department of Insurance in 2003. James R. also has a certification as a Dale Carnegie Graduate Assistant from Dale Carnegie Training. Furthermore, they are a member of the Hudson Crop 20 Million Dollar Club, an achievement awarded by the Hudson Insurance Group and Hudson Crop.