Principal Coverage Specialist, Coverage Intelligence

YOUR ROLE

As a Principal Coverage Specialist on the Coverage Intelligence team, you supply the expert judgment that our AI systems are measured against. Our agents read commercial insurance policies, quotes, and binders and assess the coverage they provide, inside the Digital Exchange, powered by DeX ai. You review that output the way an experienced underwriter, claims coverage professional, or broker would, confirm or correct it, and help build the trusted datasets that tell us how accurate the system is. Your job is to adjudicate the cases that matter, catch what the system misses, and explain why. You will partner with the Coverage Ontology Lead and work alongside our QA / Evaluation Engineer.

WHAT YOU'LL DO

• Review AI-extracted coverage data (limits, sublimits, deductibles and retentions, forms schedules, endorsements, exclusions, and conditions) against the source documents and confirm or correct it.
• Adjudicate AI-assisted labels on coverage comparisons and assessments, prioritizing the cases flagged as uncertain or disputed.
• Label how carrier wording differs from ISO standard forms and whether each difference broadens, restricts, or does not change coverage.
• Help build gold-standard evaluation sets for general liability, BOP, and workers compensation first, with other lines to follow.
• Follow and help refine labeling guidelines; flag ambiguous cases and recurring system errors to the Coverage Ontology Lead.
• Participate in calibration sessions with other reviewers to keep judgments consistent.
• Other duties and responsibilities as assigned.

YOUR LOCATION
This is a fully remote role, with the exception of onboarding and optional in-office events.

S****kills & Experience

• 7+ years' experience in commercial insurance as a coverage litigation attorney, commercial lines product developer, or claims coverage specialist.
• Strong working knowledge of ISO commercial general liability, businessowners, and workers compensation forms and common endorsements.
• Able to read a policy, quote, or binder and identify precisely what is covered, what is excluded, and how it differs from a standard form.
• Meticulous and consistent, with the patience to review a high volume of items without losing accuracy.
• Comfortable working in web-based review tools and Google Sheets or MS Excel.
• Clear written communication, especially in explaining why a coverage judgment is correct.
• Reliable availability for the agreed weekly hours, working remotely with minimal supervision.
• Juris doctor (preferred)
• Property, umbrella and excess, and professional lines knowledge (preferred)
• CPCU, AINS, or similar designations (preferred)
• Prior experience reviewing AI or automated output (preferred, not required)

Physical Requirements

• Must be able to sit/stand/walk for prolonged periods of time (up to 8 hours per day), at a desk working on a computer.
• Must be able to use standard office equipment for extended periods of time, including but not limited to, a mouse, keyboard, phone and video conferencing.

Bold Penguin is the premier digital broker for commercial insurance. Their technology expands top-of-funnel demand and increases yield for enterprise partners. Through digital distribution, wholesale capabilities, and AI-driven insights, they transform the lifecycle of both simple and complex risks, from prospecting to placement.

Benefits

We offer competitive compensation and progressive benefits that include:

• Medical, Dental, and Vision
• Flexible PTO Policy
• 401(k) with a company match
• Employee Assistance Program
• Parental Leave
• Disability and Life Benefits

Stay connected to the Glacier. We have great SLACK channels for work and play. We also like to video conference and hold all-hands "Waddles" regularly.

Penguin bling. Like swag themed after a certain Antarctic bird? Just. You. Wait.

Bold Penguin believes in inclusion. That’s why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. To learn more about our results-focused culture and employee-focused perks, read more on our careers page.