Excess & Specialty Insurance Underwriter (Contract)

About OpenTrain

OpenTrain is the #1 platform for people starting and growing careers in AI training and data labeling. The platform helps independent contributors discover projects, build a unified AI training portfolio, and apply quickly to specialized freelance roles.

We focus on durable freelance careers that let experts contribute real-world domain knowledge to how AI systems behave while maintaining flexibility and control over work.

Why AI training work matters

AI models learn from examples and expert feedback prepared by people. Experts who contribute underwriting judgment shape how commercially focused AI systems interpret policy language, assess coverage boundaries, and reason about risk.

This work is remote and flexible, often part-time, and a direct way to share industry expertise while earning competitive hourly pay.

The role

OpenTrain is recruiting an Insurance Underwriter — Excess & Specialty to contribute expert underwriting judgment to AI training data. This is a contractor, part-time role expected to average 20+ hours per week.

You will work on text-based tasks that require deep knowledge of US commercial insurance, excess casualty, umbrella coverage, and specialty lines to evaluate and generate high-quality training content.

• Employment type: Contractor, Part-time.
• Time commitment: 20+ hours/week.
• Compensation: $55–$70 USD per hour.
• Work location: Remote; worldwide applicants accepted but must have US-market experience or familiarity.

What you'll do

Your day-to-day work centers on analyzing textual scenarios, policy language, and coverage questions to produce clear evaluations, ratings, and explanatory text that trains models to reason about insurance.

• Review complex commercial and specialty risk scenarios in the US insurance market.
• Analyze, interpret, and structure coverage for excess and specialty lines.
• Assess policy language and provide nuanced feedback on policy interpretation and coverage analysis.
• Identify risk factors and apply sound underwriting judgment to ambiguous or novel cases.
• Contribute real-world insights and short written explanations that become labeled training data.
• Share trends and insight into emerging risks and innovations in excess and specialty insurance.

Requirements

Candidates must meet the core underwriting and communication requirements below; we will verify experience and domain fit during screening.

• 4–5+ years of underwriting experience in commercial lines, specialty insurance, excess casualty, or umbrella products.
• Strong understanding of commercial P&C, liability coverage, and policy evaluation best practices.
• Demonstrated expertise in policy interpretation, insurance compliance, and comprehensive coverage analysis.
• Experience working with insurance operations in complex or specialty risk environments.
• Excellent written and verbal communication skills.
• Proven track record within the US insurance market or with US-based clients and frameworks.

Helpful background

The following experience is not required but will strengthen your application and the value of your contributions.

• Prior exposure to emerging risk types, complex liability structures, or innovative coverage solutions.
• Experience collaborating on cross-functional teams or contributing to process improvement in insurance operations.
• Deep familiarity with US underwriting standards and commercial insurance practices.

How the work is delivered and how to apply

Tasks are text-based and use evaluation-rating and text-generation labels to teach models how to interpret coverage and make judgment calls. Labeling software is listed as OTHER; OpenTrain will provide project instructions, examples, and quality checks.

To apply, create or sign in to your OpenTrain profile, submit your underwriting background and availability, and highlight representative examples of commercial/specialty underwriting work or decisions. Successful applicants will complete a brief domain-focused qualification review.

• Data type: Text; label types: Evaluation rating and text generation.
• (project-specific tools provided).
• Interview/qualification will test policy interpretation and written explanation skills.