Underwriting AI Analyst

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.

Underwriting AI Analyst

(Reports to Head of AI Business Solutions – Reinsurance Underwriting)

Role Overview

The Underwriting AI Analyst supports the design, development, and deployment of AI-enabled underwriting capabilities. This role focuses on delivering high-quality analysis, preparing and validating data, and working directly with underwriting teams to ensure AI outputs are practical, accurate, and aligned to business needs.

Key Responsibilities

• Deliver analytical support for AI-driven underwriting use cases, including data preparation, validation, and output testing
• Partner with underwriters to refine use cases, ensuring outputs are relevant, explainable, and actionable
• Support the adaptation of AI solutions across multiple lines of business, maintaining consistency in approach and outputs
• Assist in testing, tuning, and improving AI models and prompt-driven workflows
• Coordinate across multiple initiatives to ensure progress, alignment, and timely delivery
• Contribute to the development of repeatable analytical frameworks and data standards

Qualifications

• 3–7 years of experience in analytics, insurance, or consulting
• Strong analytical and problem-solving capabilities with attention to detail
• Experience working with data tools (Excel, SQL, Python or similar)
• Ability to operate across multiple priorities in a fast-paced environment
• Strong communication skills with the ability to work directly with business stakeholders

What Good Looks Like

• Consistent delivery of high-quality analytical outputs supporting underwriting decisions
• AI use cases are implemented faster and with fewer rework cycles
• Improved data quality and reliability of AI-driven insights
• Strong working relationships with underwriting teams, driving adoption and trust

This role is contract-to-hire and can be based in NYC, Stamford, CT or London

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