Senior AI Underwriter

Honeycomb Insurance At Honeycomb, we're not just building technology; we’re reshaping the future of insurance. In 2025, Honeycomb was recognized by Dun & Bradstreet as “ Top 10 Best Start Up Companies to Work For ” in Israel, named by LinkedIn as “ Top 10 Startups in Chicago ”, and Newsweek’s " Greatest Startup Workplaces in America, 2025 ". Through the first half of 2026 we’ve been recognized on Inc. Magazine’s " Best Workplaces " List and Forbes " Fintech 50 ". How did we earn these honors? Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 6 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another. With over $100B in insured assets, Honeycomb operates across 23 states, covering more than 65% of the U.S. population and increasing its coverage. If you’re looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day - Honeycomb might be exactly what you’ve been looking for. AI Underwriter The Role As an Underwriter on our AI Team, you'll sit at the intersection of deep insurance expertise and next-generation technology. You'll be a critical voice in researching, developing, validating, and monitoring AI-driven risk assessment models — helping ensure they reflect real-world underwriting judgment and produce accurate, defensible outcomes. You'll have the opportunity to contribute to some of Honeycomb's most exciting technical initiatives, including: Computer Vision — helping evaluate and validate AI systems that analyze property imagery for risk assessment purposes. Generative AI — informing the development of AI-powered tools that assist in quote generation, risk narratives, and underwriting workflows. Predictive Modeling — contributing your underwriting expertise to proprietary risk models, helping drive more accurate and data-driven outcomes across our book of business. What You’ll Do Partner closely with AI researchers and engineers throughout the full model lifecycle — from early research and development through post-production monitoring. Translate complex underwriting guidelines into clear, consistent property assessments that inform and improve AI models. Conduct in-depth property reviews to identify gaps or weaknesses in current AI models and recommend improvements. Supervise labeling teams to ensure accurate property classification in production models. Provide training and ongoing guidance to annotation teams; perform continuous quality assurance on annotation projects. Assist in the discovery and evaluation of new and revised AI models, contributing underwriting subject matter expertise. Maintain open, proactive communication across underwriting and AI teams. Take on special projects and assignments as the team's needs evolve. Basic Requirements 4+ years of underwriting/insurance experience (commercial preferred) Bachelor’s degree or equivalent education/experience preferred Retail agency relationship preferred Curiosity, hardworking, self-accountable, positive attitude, humble and fun Have an opinion, share your opinion and be open to other opinions Passion to obtain, retain and employ knowledge – as well as share knowledge Excellent verbal and written communication skills Strong analytical skills and attention to detail Benefits: Salary: $100,000 - $120,000 ISO stock options Medical, dental, and vision coverage for you and your dependents HSA with company contributions 401(k) with employer match Flexible time off 10 company-paid holidays Paid family leave Honeycomb is committed to fair and equitable compensation practices. The base salary range listed in each job posting represents our goo