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Harold Cutler is an experienced transportation risk specialist currently working at Prestige Trucking Insurance since November 2021, where responsibilities include advising companies on fleet management, risk exposure, and insurance cost reduction. Prior to this role, Harold served as an agent at New York Life Insurance Company from December 2017 to November 2021 and held the position of Senior Managing Director at Stockbridge Insurance Group from May 2010 to December 2017, specializing in Medicare products and health planning. Additional experience includes roles such as Exclusive Financial Specialist at Allstate Financial Services, Director of Sales at Stockbridge Consulting Group, District Sales Manager at Aflac, and Financial Advisor at Merrill Lynch. Harold is an alumnus of Florida International University.