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

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