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Director/Lead – Product Management, Gen AI Underwriting

Director – Product Management (Gen AI Underwriting)

Partnering with Oliver James | Regional Technology Hub

The Mandate

Oliver James has been exclusively retained by a high-growth, pan-Asian insurance disruptor to appoint a Director of Product Management focused on Generative AI Underwriting.

Our client is moving beyond the “experimental” phase of AI; they are currently building a world-class technology team dedicated to deploying Gen AI products directly into the underwriting production engine. This role reports directly to the Group Chief Product & AI Officer and is a critical hire for their regional digital transformation strategy.


The Role

As the Product Lead for this domain, you will be responsible for the end-to-end lifecycle of AI-driven underwriting tools across multiple markets. You will bridge the gap between complex data science and real-world risk assessment, ensuring that Gen AI becomes a core competitive advantage for the group.

Key Focus Areas:

  • Production-Scale Gen AI: Architect and ship LLM-based products that automate unstructured data processing (medical/financial) and assist underwriters in real-time decision-making.

  • Strategic Roadmap: Define how Gen AI will evolve the group’s risk appetite and operational efficiency over a 3-year horizon.

  • Cross-Functional Leadership: Lead a high-performing squad of engineers and data scientists, while collaborating with Group Underwriting to ensure model “explainability” and regulatory compliance.

  • Regional Impact: Localize AI solutions for diverse markets across Asia, balancing global scalability with local regulatory requirements.


The Profile

Our client is looking for a unique blend of Insurance domain authority and Modern Product craft:

  • Product Mastery: Extensive experience leading technical product teams, specifically within AI/ML. You must have experience shipping products to a live production environment.

  • Underwriting Expertise: A deep understanding of Life or Health underwriting workflows and the nuances of risk selection.

  • Technical Fluency: A strong grasp of Generative AI architectures (RAG, prompt orchestration, fine-tuning) and how to mitigate the risks associated with LLMs in a regulated industry.

  • Executive Presence: The ability to influence at the C-Suite level and translate “AI hype” into concrete, ROI-driven business outcomes.