Senior Commercial Broker, Brokerage Intelligence

About the role

Turn expert commercial brokerage judgment into the systems, training, and product recommendations that define how Harper brokers insurance. The hardest brokerage decisions rarely begin as clean rules; they live in the judgment of people who have seen difficult risks, thin submissions, unusual coverage structures, and market exceptions. Your job is to make that judgment teachable, testable, and reusable across Harper. You will work deeply with product, engineering, operations, and insurance teams to build the brokerage infrastructure behind the work: the workflows people follow, the standards AI systems are evaluated against, the training that changes behavior, and the feedback loops that make the whole operation improve. Harper is building an AI‑native brokerage, and that only works if expert judgment becomes something people and systems can learn from.

Responsibilities

• Partner closely with product and engineering to turn brokerage judgment into useful tools and reliable AI evaluations.
• Bring the insurance standard and evidence; define brokerage product requirements.
• Train and evaluate AI systems: build realistic cases, expected outcomes, grading standards, and failure examples; review AI behavior against source evidence and expert judgment.
• Design and evaluate brokerage workflows: encode how information, decisions, exceptions, and handoffs should move through account processes.
• Own the brokerage learning standard: create content, cases, worked examples, decision standards, and effectiveness measures.
• Run the expert feedback loop: stay close to frontline work, difficult cases, market responses, and user behavior; separate one‑off exceptions from recurring patterns and route each to the right product, process, or training change.
• Set evidence standards: ensure recommendations and decisions remain traceable to the real application, document, communication, quote, or market response that supports them.
• Raise the quality bar: identify where a workflow produces inconsistent judgment, where an AI system sounds right but is wrong, and where a person cannot tell what to do next; redesign the system until the standard is clear and usable.

Requirements

• Substantial commercial brokerage, wholesale brokerage, or placement experience across complex small and middle‑market accounts.
• Built submission strategies, negotiated difficult terms, and seen enough real outcomes to know where written process ends and expert judgment begins.
• Understand general liability, property, workers' compensation, commercial auto, umbrella, and specialty coverage well enough to recognize the material facts, tradeoffs, and exception paths.
• Excited to use brokerage expertise to build products, systems, and standards rather than personally produce accounts.
• Able to turn tacit judgment into precise instructions, worked examples, and reviewable evaluations without pretending every decision is deterministic.
• Able to teach experienced people without talking past them, and translate insurance practice clearly for product and engineering partners.
• Test own assumptions against source evidence and change the standard when the evidence proves it wrong.
• Curious about AI, comfortable examining its failures in detail, and motivated by making expert work more consistent and scalable.
• Based in New York or San Francisco, or ready to relocate to one of those offices.
• Not suitable for candidates who want to personally produce and bind individual accounts, prefer to keep expert judgment in their own head, treat documentation as a summary written after the real work, want AI to sound convincing more than correct, prefer remote individual practice, or are unwilling to revisit familiar brokerage habits when challenged.

Benefits

• Health insurance
• Dental insurance
• Vision insurance
• Office‑specific benefits set by working location

Pay

Compensation range: $150,000 – $200,000 per year.