[Remote] AI Evaluator - Insurance Domain | Remote

Note: The job is a remote job and is open to candidates in USA. Crossing Hurdles is seeking Insurance Experts with a focus on underwriting and actuarial analysis. The role involves translating insurance workflows into structured tasks for AI systems and evaluating AI-generated outputs for accuracy and relevance.

Responsibilities

• Translate real-world insurance workflows into structured tasks for AI systems
• Evaluate AI-generated outputs for accuracy, logical reasoning, and business relevance
• Work on use cases including underwriting, claims, actuarial analysis, and insurance operations
• Identify gaps, edge cases, and failure modes in model performance
• Clearly document assumptions, thought processes, and decisions
• Provide structured feedback to improve AI performance and outputs

Skills

• Minimum 5 years of professional experience in the insurance sector
• Recent, hands-on experience as an Underwriter, Risk Specialist, or Actuary
• Strong understanding of real-world insurance workflows and processes
• Detail-oriented with the ability to evaluate nuanced, real-world scenarios
• Comfortable working independently in a fast-paced, remote environment

Benefits

• Work is primarily asynchronous, allowing for flexible scheduling
• Minimal required meetings (typically optional office hours)
• Seamless day-to-day collaboration and task management handled via Slack and internal platforms

Company Overview

• Crossing Hurdles connects skilled professionals with opportunities across leading AI training platforms and high-growth companies. It was founded in 2022, and is headquartered in , with a workforce of 11-50 employees. Its website is https://www.crossinghurdles.com/.

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