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Gary Bare has extensive work experience in the insurance industry. Gary began their career at Allstate as a Sales Agent, where they marketed personal lines, life insurance, and commercial lines to the public. Gary then joined General Accident/Silvey Companies as a Commercial Lines Floor Manager, overseeing the day-to-day activities of commercial underwriters. After that, Gary worked at Missouri Employers Mutual as an Underwriter, evaluating risk for mono line Worker's Compensation policies. Gary then moved to State Auto Insurance as a Senior Commercial Underwriting Specialist - Field Underwriter, responsible for underwriting various lines of insurance for accounts in the Construction, Manufacturing, Transportation, and Services sectors. Prior to their current role, Gary worked at CNA Insurance as a Senior Underwriting Specialist - Middle Market, underwriting Property, General Liability, Inland Marine, Business Auto, Umbrella, and Workers' Compensation policies. Currently, Gary is employed at Winter-Dent & Company as Senior Commercial Line Underwriter / Risk Management, where they are responsible for underwriting various lines of insurance and managing risk for clients in the Construction, Manufacturing, Transportation, and Commercial Agri-Business sectors.

Gary Bare completed their General Studies education from MHS between 1974 and 1977. Later, they obtained a certification as a Certified Workers' Compensation Advisor from the Institute of Workers' Compensation Professionals. Additionally, Gary received training in Insurance from The Institutes Risk & Insurance Knowledge Group. In 2010, they obtained the State of Missouri E & S License and State of Missouri P & C Licenses from the Missouri Division of Insurance. Gary also holds the CWCA certification, although the institution and date of acquisition are unknown.