[Hiring] Principal Commercial Insurance Coverage Specialist @Bold Penguin

Role Description

Own the coverage ontology end to end, including the entity model, clause taxonomy, and the relationships among coverage grants, exclusions, conditions, definitions, limits, sub limits, retentions, and triggers.

• Build and maintain ISO rubrics that define how standard form language is classified, scored, and compared, and extend those rubrics to AAIS, proprietary, and manuscript wording.
• Establish and steward the form, edition, and endorsement registries, including carrier variants, effective dates, supersession, versioning, review cadence, change control, and deprecation.
• Develop form templates and delta structures so a carrier's wording can be diffed against a base form and the coverage consequence of each variation is explicit rather than implied.
• Build NAICS and class of business overlays that connect exposure to the coverage a risk in that class should be expected to carry, and keep those overlays current as appetite and market wording shift.
• Define the coverage logic behind agent use cases: multi-carrier quote comparison, quote to bound and issued policy verification, broker proposal preparation, and tower analysis across attachment points, follow form and differing terms, drop down, and exhaustion.
• Serve as ground truth for model development. Build gold standard labeled sets and evaluation sets for clause extraction, classification, comparison, and adjudicate disputed output.
• Set the accuracy bar for coverage output, define what a material miss looks like, and drive the review loop that closes the gap between agent output and expert judgment.
• Partner with product management and engineering to carry the ontology into schemas, data contracts, prompts, and interfaces, and to keep the model in the product aligned with the model of record.
• Identify gaps between the ontology and real customer requirements across Submission Ingestion, Market Intelligence, Market Access, and Coverage Intelligence, and carry durable requirements into the roadmap.
• Partner with Legal, Compliance, and Security on AI governance, documentation, and disclosure standards for coverage analysis, including how conclusions are sourced and explained.
• Work directly with brokers, underwriters, and carrier technical staff to validate the ontology against how coverage decisions get made, and to pressure test it against edge cases.
• Train and mentor coverage analysts and product staff so ontology fluency is shared across the team and does not depend on one person.
• Represent Bold Penguin externally with partners, carriers, and industry forums as a credible coverage and technical expert.
• Additional duties and responsibilities as assigned.

Qualifications

• 10+ years' experience in commercial insurance coverage, gained as coverage counsel, a claims coverage leader, a technical underwriter, or a broker side coverage or placement specialist.
• JD preferred.
• Deep working knowledge of ISO standard forms and endorsements across lines, including general liability, property, commercial auto, umbrella and excess, workers compensation, professional, cyber, and management liability.
• Demonstrated ability to read manuscript and surplus lines wording and articulate precisely how it differs from a standard form and why that difference matters.
• Practical experience with layered and shared programs, including follow form and differing terms, quota share participations, attachment and exhaustion, and the coverage consequences of a mismatched tower.
• Experience building or stewarding taxonomies, ontologies, coverage rubrics, or data dictionaries over time, not just at launch. Equivalent experience imposing structure on unstructured policy content will be considered.
• Familiarity with NAICS and commercial class code systems and how class drives coverage expectations.
• Working fluency with AI and machine learning concepts, including how large language models handle document analysis, where they fail, and how output quality is measured.
• Comfort reviewing and correcting model output at scale, and the patience to turn recurring errors into a durable fix in the ontology.
• Proficient with Google Sheets and MS Excel, including advanced formulas for data analysis.
• Excellent written and verbal communication skills, with the ability to explain a coverage position to engineers and a technical design to executives.
• Ability to synthesize information from multiple sources to understand and explain complex concepts.
• Familiarity with AI governance, model risk, and insurance regulatory expectations is a plus.
• Works autonomously with minimal direction, sets a clear path through ambiguity, and holds a high bar without needing direct authority.
• Deeply curious about coverage, about the market, and about what the technology can and cannot do.
• Thrives on the energy of a start-up: comfortable with pace, changing priorities, and building the function while running it.

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.

Benefits

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