Deputy Underwriting AI Solutions

Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world's leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London. OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth. OdysseyRe is rated A+ (Superior) by AM Best and AA

• (Very Strong) by Standard and Poor's. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH. Deputy
• Underwriting AI Solutions (Reports to Head of AI Business Solutions
• Reinsurance Underwriting) Role Overview The Deputy
• Underwriting AI Solutions is responsible for scaling and operationalizing AI-enabled underwriting capabilities.

This role focuses on taking proven AI solutions and making them consistent, controlled, and production-ready across multiple business units and geographies. Key Responsibilities Lead and manage AI-enabled underwriting workstreams in active business use Drive the productionization of AI solutions in partnership with IT, data, and architecture teams Establish and enforce repeatable frameworks for AI-driven underwriting analysis and decision support Ensure AI outputs are consistent, explainable, and aligned to underwriting standards and risk appetite Implement governance and control mechanisms, including validation, testing, and monitoring of AI outputs Support rollout and adoption across multiple lines of business and regions Act as the primary bridge between underwriting, data, and technology teams to ensure alignment and delivery Qualifications 10+ years of experience in insurance, analytics, or technology Strong understanding of underwriting workflows, decision-making, and risk considerations Experience with data platforms, analytics, or AI/ML solutions Proven ability to translate business needs into scalable, production-ready solutions Strong stakeholder management and communication skills What Good Looks Like AI capabilities are embedded into underwriting workflows and used consistently Solutions are stable, repeatable, and production-ready with minimal operational risk Clear governance and controls are in place for AI usage Successful expansion of AI capabilities across multiple business units without fragmentation This role can be based in NYC, Stamford, CT or London We are an E-Verify employer

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