Senior Auto Claims Adjuster - Freelance AI Trainer

About the Role

The day-to-day responsibilities of this position will involve working closely with AI systems to design and implement tests that push the limits of their decision-making capabilities. This will include creating realistic scenarios that mimic real-world claims, identifying potential flaws in the system's logic, and providing detailed feedback that contributes to the continuous improvement of the AI. Given the project-based nature of this work, flexibility, adaptability, and the ability to quickly grasp new concepts and technologies are essential.

What You Will Do

• Evaluate AI-generated auto insurance claims decisions for accuracy, coverage correctness, and regulatory compliance
• Design realistic First Notice of Loss (FNOL) scenarios to test the robustness of AI agents
• Create test cases for coverage-scope decisions that require domain knowledge for correct assessment
• Develop and grade fraud-flagging scenarios using structured reason codes for Special Investigation Unit (SIU) referral
• Build subrogation test cases applying state-specific negligence rules to assess recovery likelihood
• Develop supervisor-escalation scenarios to ensure AI agents recognize authority-limit thresholds
• Draft and evaluate reservation-of-rights letter scenarios, ensuring language remains within the bad-faith line
• Validate coverage-limits math when multiple endorsements stack on a single claim
• Document test cases clearly, including correct answers, policy citations, and payout calculations
• Collaborate with project teams to implement feedback and improve AI system performance
• Participate in project meetings to discuss progress, challenges, and future directions

What We Are Looking For

• Degree in Finance, Business, Insurance, or a related field, or equivalent professional experience
• A minimum of 3+ years of hands-on auto claims adjusting, examining, or supervisory experience at a U.S. carrier, independent adjusting firm, or SIU team
• Ability to make coverage decisions without referencing manuals, demonstrating deep domain knowledge
• Familiarity with U.S. state-specific rules, including comparative vs. contributory negligence states and state adjuster licensing requirements
• Experience reading full auto policy documents with citation discipline
• Proficiency in computing payout math involving deductibles, sub-limits, and layered endorsements in Excel or equivalent
• Awareness of the bad-faith line and adjuster authority-limit culture
• Associate in Claims (AIC), Chartered Property Casualty Underwriter (CPCU), or similar credentials are a strong positive
• Strong written English skills (C1+ level)

Nice to Have

• Experience with AI systems or machine learning technologies
• Previous work in a freelance or project-based environment
• Familiarity with agile project management methodologies
• Certification in data analysis or a related field

Benefits and Perks

• Opportunity to work on cutting-edge AI technology in the insurance sector
• Flexible, project-based work arrangement allowing for a better work-life balance
• Competitive hourly rate with potential to earn up to $60 per hour equivalent, depending on contribution level and project requirements
• Professional development opportunities through exposure to new technologies and methodologies
• Collaboration with a team of experienced professionals in the insurance and AI sectors
• Access to a platform that offers a variety of projects, allowing for diversity in work and continuous learning
• Remote work stipend to support home office setup and productivity
• Health and wellness programs to support mental and physical health

• Ensure your CV is tailored to highlight your claims adjusting experience and any relevant certifications like AIC or CPCU.
• Brush up on your Excel skills, particularly in calculating payouts and managing complex spreadsheets.
• Familiarize yourself with U.S. state-specific insurance regulations and the concept of comparative vs. contributory negligence.
• Prepare examples of complex claims you've managed in the past, focusing on your decision-making process and how you've handled unique scenarios.
• During interviews, be ready to discuss your experience with AI systems, if any, and how you adapt to new technologies.
• Consider building a portfolio of your work, including documents or scenarios you've developed for testing AI systems, to demonstrate your capabilities.
• When negotiating salary, highlight your experience and the value your domain knowledge brings to AI training and development.