Senior Underwriter, Retail Cyber & Technology E&O
Liberty Mutual Insurance
Chicago, IL · Posted September 23, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about finance jobs
- Best cities for finance jobs #1 New York (1,932 openings)
- Best cities for finance pay after cost of living #1 San Mateo ($162k)
- Most requested AI skills in finance jobs #1 AI tools in daily work (4.3%)
- AI tools named most often in finance jobs #1 Claude (0.55%)
- Employers with the most finance jobs #1 Amazon (475 roles)
Pay compared with the market
This listing does not state pay. Across 83 open senior underwriter listings that state pay, the middle half runs $110,000 to $146,500 and the median is $130,000.
Listed pay is what employers advertise, not what people are paid.
How AI is used in this kind of work
AI use among insurance underwriters is little observed so far. Measured exposure for insurance underwriters: 6% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
About the job
Build relationships with senior, market-leading brokers and key agents, maintain a strong market presence and look for ways to strengthen existing relationships and develop new ones. Explain key coverage differences with a high degree of detail. Provide meaningful input into business and marketing planning, including data-driven insights from portfolio analysis. Collaborate across departments on projects that drive underwriting and process excellence, working effectively with underwriting support, claims, actuarial and directors of underwriting across North America. Stay current on key legal cases, legislation and regulation affecting your area of underwriting expertise, and share that knowledge through thought leadership. Degree in Business or equivalent typically required A minimum of 7 years expected, typically 5 years or more, of progressive underwriting experience and/or other related business experience CPCU or professional insurance designation preferred Proven analytical ability to evaluate and judge underwriting risks within scope of responsibility Demonstrated ability to communicate complex analyses and information in understandable written and/or oral directives to other persons in the organization for underwriting or training purposes Demonstrated effective communication and interpersonal skills in dealing with internal and external stakeholders Must demonstrate comprehension of most complex technical underwriting issues and be capable of defining and implementing necessary underwriting and administrative processes/workflows to properly manage or administer those issues Proven track record of developing and underwriting profitable business