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Salary: USD 160,000 - 220,000 / annual
Bold Penguin is a digital broker for commercial insurance powered by AI. As Principal Commercial Insurance Coverage Specialist, you will own the coverage ontology that underpins the Digital Exchange and its Coverage Intelligence agents. You are the authority on how insurance coverage is represented, reasoned about, and applied at scale.
You will own the end-to-end coverage ontology, including the entity model, clause taxonomy, and relationships among coverage grants, exclusions, conditions, definitions, limits, sub-limits, retentions, and triggers. You will build and maintain ISO rubrics that classify and compare standard form language, and extend those rubrics to AAIS, proprietary, and manuscript wording. You will establish and steward form, edition, and endorsement registries with proper versioning, change control, and deprecation processes.
You will develop form templates and delta structures so carrier wording variations can be diffed against base forms with explicit coverage consequences. You will build NAICS and class of business overlays connecting exposure to expected coverage, keeping them current as market appetite and wording shift. You will define the coverage logic behind key 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, differing terms, drop down, and exhaustion.
You will serve as ground truth for model development, building gold standard labeled and evaluation sets for clause extraction, classification, and comparison. You will set accuracy bars for coverage output, define material misses, and drive the review loop closing gaps between agent output and expert judgment. You will partner with product, engineering, and data science to carry the ontology into schemas, data contracts, prompts, and interfaces, keeping the production model aligned with the model of record.
You will identify gaps between ontology and real customer requirements across Submission Ingestion, Market Intelligence, Market Access, and Coverage Intelligence, carrying durable requirements into the roadmap. You will partner with Legal, Compliance, and Security on AI governance, documentation, and disclosure standards for coverage analysis. You will work directly with brokers, underwriters, and carrier technical staff to validate the ontology and pressure-test it against edge cases. You will train and mentor coverage analysts and product staff to build ontology fluency across the team. You will represent Bold Penguin externally as a credible coverage and technical expert.
REQUIREMENTS:
- 10+ years' experience in commercial insurance coverage as coverage counsel, claims coverage leader, technical underwriter, or broker-side coverage/placement specialist. JD preferred.
- Deep working knowledge of ISO standard forms and endorsements across lines: 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 standard forms and why those differences matter.
- Practical experience with layered and shared programs, including follow form and differing terms, quota share participations, attachment and exhaustion, and coverage consequences of mismatched towers.
- 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 patience to turn recurring errors into durable ontology fixes.
- Proficient with Google Sheets and MS Excel, including advanced formulas for data analysis.
- Excellent written and verbal communication skills, with ability to explain coverage positions to engineers and technical designs 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 clear paths through ambiguity, and holds high bars without needing direct authority.
- Deeply curious about coverage, the market, and what technology can and cannot do.
- Thrives in startup environment: comfortable with pace, changing priorities, and building the function while running it.
