Specialty Insurance Underwriter/Coverage Attorney/Consultant/Professional (Contract)

Overview

This part-time, contract role focuses on applying expertise in excess and specialty (E&S) insurance to help evaluate and improve AI that reads specialty insurance policies and produces structured, decision-ready data.

You will work directly with an engineering team to identify where the AI falls short, annotate and review insurance documents and AI outputs, and help define rubrics and benchmarks for quality.

Responsibilities

• Annotate policy limits structures within excess policies, including limits, sublimits, retentions, attachment points, and how the layers stack.
• Review and render coverage conclusions by analyzing an insuring agreement and its exclusions and producing structured conclusions about how coverage responds to described scenarios.
• QA and correct labeled data by reviewing AI-generated output, fixing mislabeled data, and grading agent performance against what a seasoned practitioner would conclude.
• Resolve complex coverage ambiguities involving manuscript wording, follow-form excess, nested exclusions, schedules of underlying disputes, and implicit market conventions that affect whether coverage is trusted by real practitioners.
• Build evaluation rubrics by partnering with the team to design scoring criteria and review workflows for line-by-line accuracy of extractions and coverage conclusions.
• Shape how product coverage is presented by translating practitioner needs into requirements (structure, what should be shown, and what would mislead them).
• Serve as a translator between documents and engineers by explaining terminology, market conventions, and the “why” behind standard practices; flag where assumptions do not match reality across lines of business.
• Validate against expert answers by reviewing real policies, endorsements, and claims documents and specifying the correct coverages, limits, sublimits, retentions, attachment points, exclusion logic, and layer stacking so the AI can be measured and improved.

Required Experience

• USA-based.
• 3+ years of experience minimum; 5+ years strongly preferred, specifically within excess and specialty insurance.
• Experience in excess and specialty (E&S) insurance as an underwriter, coverage attorney/counsel, or consultant.

Qualifications

• Deep, hands-on specialty insurance experience (underwriting, claims, broking, or coverage counsel) and/or broad multiline experience across lines such as General Liability, Professional Liability, and related casualty and specialty lines.
• Ability to read a policy end-to-end (declarations, forms, endorsements, schedules of underlying) and explain precisely how coverage responds, including across primary and excess layers.
• Strong ability to articulate what “correct” means and the reasoning behind determinations so it can be encoded into an AI system.
• Clear communication with non-insurance experts and comfort with iterative collaboration (including explaining concepts to engineers).
• No technical background required—the focus is on judging correctness, not building AI systems.

Preferred Qualifications

• Claims experience (working as, closely alongside, or supporting claim adjusters/examiners, complex or litigated claims specialists, or claims counsel).

Compensation & Benefits

• Competitive hourly rate commensurate with experience and depth of expertise.

Engagement Details

• Part-time, contract engagement with flexible scheduling that fits your current work.
• Approximately 2–10 hours per week for an initial 3–4 months, with the opportunity to extend based on mutual interest and project needs.
• Remote-friendly, with collaboration over shared documents and working sessions with AI and product teams.

Location

• USA-based.