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Kieran J. O'Rourke has over 35 years of experience in the insurance industry. Kieran J. began their career in 1985 with Westfield Group, where they held the role of Region Executive for Business Development, managing both field and the Home Office underwriting staff. In 2002, they joined Cincinnati Insurance Co. as Regional Director, responsible for maintaining relationships with a group of independent agents operating throughout a five-county territory in Ohio. In 2004, they served as President of the Board of Public Affairs for the Village of Seville. In 2009, they took on the role of General Manager at National Interstate Insurance Company, directing the efforts of a team with P&L accountability for 10 business lines. In 2012, they joined Energi Insurance Services, Inc. as Assistant Vice President of Research & Development, responsible for numerous R&D initiatives and building specialized insurance and risk management programs. In 2016, they moved to AmTrust Financial Services, Inc. (AFSI) as Assistant Vice President of Property Underwriting, with corporate responsibility for the property book's profit, growth, and retention. In 2017, they began their current role as Vice President, Director of Underwriting at Cannasure Insurance Services, one of the leading marijuana insurance providers in the industry.

Kieran J. O'Rourke holds a Bachelor of Science in Industrial Management (Personnel) from The University of Akron. Kieran J. has also obtained certifications as a Certified Insurance Counselor, Certified Risk Manager, and Chartered Property & Casualty Underwriter.