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Harper is building an AI-native insurance brokerage platform. This role sits at the intersection of commercial insurance expertise, product strategy, and AI systems development.
You will not sell insurance, own a book, carry a sales quota, or make final account-level placement decisions. Instead, you will translate expert commercial brokerage judgment into teachable, testable systems that scale across the organization.
Key responsibilities:
- Encode brokerage judgment: Convert complex commercial insurance decisions into clear workflows, decision standards, playbooks, examples, and escalation rules that preserve nuanced expert reasoning.
- Define brokerage product requirements: Partner with product and engineering to identify high-impact brokerage problems, specify what systems must understand, and ground recommendations in real evidence.
- Train and evaluate AI systems: Build realistic test cases, expected outcomes, grading standards, and failure examples. Review AI behavior against source evidence and expert judgment; convert failures into permanent evaluations and product improvements.
- Design and evaluate workflows: Encode how information, decisions, exceptions, and handoffs move through account processes. Ensure workflows produce sound judgment without removing human decision-making from individual accounts.
- Own brokerage learning standards: Create content, cases, worked examples, decision standards, and effectiveness measures that make expert judgment teachable. Collaborate with learning and enablement teams on delivery.
- Run expert feedback loops: Stay close to frontline work, difficult cases, and market responses. Distinguish one-off exceptions from recurring patterns and route each to the appropriate product, process, or training change.
- Set evidence standards: Ensure all recommendations and decisions remain traceable to real applications, documents, communications, quotes, or market responses.
- Raise quality standards: Identify where workflows produce inconsistent judgment, where AI systems sound right but are wrong, or where people cannot determine next steps. Redesign until standards are clear and usable.
You will work closely with product, engineering, operations, insurance teams, placement teams, licensed brokers, underwriters, and account owners. You define standards; they retain final decision authority on individual accounts.
Requirements:
- Substantial commercial brokerage, wholesale brokerage, or placement experience across complex small and middle-market accounts.
- Demonstrated ability to build submission strategies, negotiate difficult terms, and understand where written process ends and expert judgment begins.
- Strong knowledge of general liability, property, workers' compensation, commercial auto, umbrella, and specialty coverage; ability to recognize material facts, tradeoffs, and exception paths.
- Ability to convert tacit judgment into precise instructions, worked examples, and reviewable evaluations without oversimplifying decisions.
- Skill in teaching experienced professionals and translating insurance practice for product and engineering partners.
- Comfort examining AI failures in detail and commitment to making expert work more consistent and scalable.
- Willingness to test assumptions against source evidence and revise standards when evidence warrants.
- Based in New York or San Francisco, or willing to relocate to one of those offices.
- Preference for in-person, cross-functional collaboration over remote individual work.
