Senior Underwriter, Midwest

Honeycomb Insurance
Chicago, IL
Remote

Who this role is best for

Candidates with LRO underwriting experience and AI proficiency will find this hybrid role in the Midwest challenging yet rewarding.

Best fit for

  • Candidates with 4+ years of underwriting experience and a strong LRO background will naturally align with this role.
    — “4+ years of underwriting/insurance experience with a strong LRO background required”
  • Individuals who thrive in a culture that values knowledge-sharing and innovation will succeed here.
    — “Passion to obtain, retain and employ knowledge – as well as share knowledge”
  • Professionals comfortable with technology-driven risk assessment and automation will excel.
    — “AI Proficiency and desire to seek automation and efficiency opportunities”

Things to consider

  • The role requires at least three days per week in the Chicago office despite being remote or hybrid.
    — “This position is remote in the Midwest or Hybrid out of our Chicago Office, 3X weekly”
  • Candidates must be prepared to travel occasionally, up to 20% of the time.
    — “Some travel as deemed necessary <20%”

How to stand out

  • Highlight your experience with risk-based decision-making and portfolio management in your resume.
    — “make risk-based decisions on referred accounts”
  • Demonstrate your ability to analyze and approve policy changes across different insurance portfolios.
    — “Analyze and approve requested policy changes across the LRO and Habitational portfolio”
  • Showcase your familiarity with state insurance regulations and ISO rules in your application materials.
    — “Maintain familiarity and compliance with state insurance regulations and ISO rules”
  • Emphasize your communication skills and ability to collaborate across teams and departments.
    — “Maintain open, transparent and supportive communications with team members and interdivisional partners”
  • Demonstrate your analytical skills and attention to detail in underwriting evaluations.
    — “Strong analytical skills and attention to detail”
Pace · SteadyCollaboration · HighAutonomy · MediumDecision Impact · Company

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • risk assessment
  • underwriting
  • portfolio profitability
  • retention
  • state insurance regulations
Typical background
underwritinginsurancerisk management

Skills & requirements

Required

UnderwritingRisk AssessmentAI ProficiencyCuriosityHardworkingPositive AttitudeCommunication SkillsAnalytical SkillsAttention To Detail

Preferred

Commercial Real Estate InsuranceSpecialty Property Experience

Stack & domain

UnderwritingRisk AssessmentAIISO RulesState Insurance RegulationsCommercial Real Estate InsuranceHabitationalLessor's Risk Only (lro)Excess LiabilityPolicy ChangesPortfolio ProfitabilityPortfolio RetentionMarketingTeam CommunicationData AnalysisReportingAuditsInspectionsCommunicationTeamworkLeadershipProblem-solvingCuriosityAttention To DetailPositive AttitudeFlexibilityInsuranceCommercial Real Estate

About the role

Original posting from Honeycomb Insurance via Greenhouse

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.

What You'll Do

Next-generation risk assessment – divesting from binary underwriting and revisioning risk selection utilizing mega data, AI and curiosity. Modernized underwriting using cutting edge technology to more accurately and quickly assess risk, price and bespoke coverage/terms to profitably grow and manage a book of business spanning Habitational and Lessor's Risk Only (LRO) package and excess liability. Honeycomb offers an environment of personal and career growth to achieve your best self through mentorship, engaging project assignments, personalized training and development, and internal and exterior exposure opportunities to expand your network and sphere of influence.

Evaluate renewal Habitational accounts for underwriting acceptability, make risk-based decisions on referred accounts, and partner with the Director of Underwriting and AVP of Renewal Underwriting to support portfolio profitability and retention.

Analyze and approve requested policy changes across the LRO and Habitational portfolio

Maintain familiarity and compliance with state insurance regulations and ISO rules for all states within assigned underwriting territory

Maintain open, transparent and supportive communications with team members and interdivisional partners

Monitor portfolio composition via reports, audits and inspections

Support marketing functions and efforts to build and promote Honeycomb

Complete special projects and assignments

Some travel as deemed necessary <20%

Basic Requirements

4+ years of underwriting/insurance experience with a strong LRO background required; Commercial Habitational and Specialty Property experience is a valued addition to that background, not a standalone requirement

Bachelor's degree or equivalent education/experience preferred

Retail agency relationship preferred

AI Proficiency and desire to seek automation and efficiency opportunities

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

This position is remote in the Midwest or Hybrid out of our Chicago Office, 3X weekly

Benefits

Salary Range: $100,000 - $120,000 (Pending Experience) + Bonus

Health Benefits

Employee options grant

401K with employer match

Flexible paid time off

Paid national holiday

Source: Honeycomb Insurance careers (Greenhouse)

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