Senior Underwriter / Risk Specialist | Remote

Role: Insurance Experts (Underwriting & Actuary) Engagement Type: Freelance/ 1099 Contractor, Remote Compensation: $100–$125 per hour Commitment: Minimum 10+ hours/week (Ideally 15–20 hours, depend upon interest and availability) Start: Immediate | 24-hour fast-track onboarding required Key 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 Required Qualifications 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 Work Style & Expectations 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. Candidates must be prepared to complete the onboarding process and initiate communication with the project team within 24 hours of receiving an offer.

The role involves translating insurance workflows into tasks for AI systems and evaluating AI outputs for accuracy and relevance. Additionally, the position requires identifying gaps in model performance and providing structured feedback.

Candidates must have a minimum of 5 years of experience in the insurance sector, with recent hands-on experience as an Underwriter, Risk Specialist, or Actuary. A strong understanding of insurance workflows and the ability to work independently in a remote environment are essential.

Identified from the job description. Confirm important requirements above.

• Underwriting
• Risk Assessment
• Actuarial Analysis
• Insurance Workflows
• AI Evaluation
• Documentation
• Feedback
• Independent Work
• Detail-Oriented
• Fast-Paced Environment

• Finance & Accounting
• Consulting
• Technology

Minimum experience

5+ years

Posting language

English

Working hours

20 hours per week

Seniority

Associate

Application method

Direct apply is available