Deputy Underwriting AI Solutions
Listed on 2026-05-09
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IT/Tech
AI Engineer (Applied/Software)
Deputy Underwriting AI Solutions
Date: May 6, 2026
Location: Stamford, CT, US London, GB New York, NY, US
Company: Odyssey
Odyssey Reinsurance Company (Odyssey Re) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. Odyssey Re 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), Asia Pacific and London.
Odyssey Re 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.
Odyssey Re 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 work streams 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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Nearest Major Market:
Bridgeport
Nearest Secondary Market:
Danbury
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