Senior AI Underwriter

Senior AI Underwriter

Austin, TX; Chicago, IL; Denver, CO; East Coast - Remote; Midwest - Remote; New York City, NY

Honeycomb

At Honeycomb, 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 and named by LinkedIn as "Top 10 Startups in Chicago".

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 5 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 $55B in insured assets, Honeycomb operates across 20+ major states, covering 60% 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.

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 good faith estimate of what we expect to pay for the role. Actual compensation may vary based on skills, experience, education, and location, as well as internal alignment and market factors.