Deputy Underwriting AI Solutions

Odyssey • Stamford, CT

5d • Hybrid

About The Position

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.

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.

Requirements

• 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

Nice To Haves

• 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

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

Benefits

• excellent benefits
• strong commitment to providing training and opportunities for our staff
• innovative, enriching environment
• great pride in their career growth

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed