Demo

Senior Underwriter, Middle Market

Sompo
Chicago, IL Full Time
POSTED ON 4/5/2026
AVAILABLE BEFORE 5/12/2026
Are you looking for your next opportunity?

Sompo has a unique opportunity for a Senior Underwriter on our Middle Market team.

Our Middle Market Underwriting team offers diverse multi-line capabilities targeted at select industry verticals such as real estate, hospitality, financial institutions, professional services, technology, and manufacturing. We work through a network of retail brokers who share our commitment to long-term partnerships built on a strong service proposition.

Location: This position can be based out of our Chicago, IL office. We strive for collaboration, which is why we offer a work environment where our employees thrive and develop long-lasting careers.

Our Business, Your Impact, Our Opportunity

What you’ll be doing:

  • Drive acceptable submission activity and quickly determine acceptability of risk in accordance with Sompo guidelines and standards
  • Demonstrate technical expertise and product knowledge in Middle Market P&C Insurance (Property, General Liability, Workers’ Compensation, Automobile, Umbrella)
  • Good understanding of pricing components and rating methodology; prices risk based on financial and competitive analysis. As well as using sophisticated pricing models across various structures: guaranteed cost, captives, SIRs, deductibles, etc.
  • Use all appropriate underwriting tools, disciplines, and knowledge of strategies to ensure underwriting guidelines are followed
  • Exhibits technical underwriting skills through strategic, thorough account reviews and file documentation
  • Prepares or analyzes information on adverse underwriting decisions, rate appeals, underwriting requirements, status, and declinations to drive results within the assigned territory
  • Adheres to guidelines and underwriting discipline to minimize exposure and appropriately price risks
  • Keeps current on state/territory issues, regulations, and trends, in addition to market conditions
  • Develop and maintain strong relationships with brokers, serving as the primary underwriting resource and point of contact
  • Attend client/broker meetings, lunches, dinners, and other social outings as applicable and willingness to travel to aggressively market assigned territory

What You’ll Bring

  • Minimum 3 years of underwriting authority/insurance experience
  • Experience in working, producing, and underwriting all sizes of accounts with large brokerage houses, agents, and specialty retailers
  • Experience of successfully underwriting, quoting, and binding profitable business
  • Established relationships with brokers and agents on both a regional and national level.
  • Strong negotiation skills, Strong attention to detail, and excellent oral and written communication skills
  • Team player with grit, and collaborative by nature
  • Bachelor’s Degree preferred

Salary Range: $100,000 - $170,000 Actual compensation for this role will depend on several factors including the cost of living associated with your work location, your qualifications, skills, competencies, and relevant experience.

At Sompo, we recognize that the talent, skills, and commitment of our employees drive our success. This is why we offer competitive, high-quality compensation and benefit programs to eligible employees.

Our compensation program is built on a foundation that promotes a pay-for-performance culture, resulting in higher incentive awards, on average, when the Company does well and lower incentive awards when the Company underperforms. The total compensation opportunity for all regular, full-time employees is a combination of base salary and incentives that gets adjusted upfront based on overall Company performance with final awards based on individual performance.

Summary

We continuously evaluate and update our benefit programs to ensure that our plans remain competitive and meet the needs of our employees and their dependents. Below is a summary of our current comprehensive U.S. benefit programs:

  • Two medical plans to choose from, including a Traditional PPO & a Consumer Driven Health Plan with a Health Savings account providing a competitive employer contribution
  • Pharmacy benefits with mail order options
  • Dental benefits including orthodontia benefits for adults and children
  • Vision benefits
  • Health Care & Dependent Care Flexible Spending Accounts
  • Company-paid Life & AD&D benefits, including the option to purchase Supplemental life coverage for employee, spouse & children
  • Company-paid Disability benefits with very competitive salary continuation payments
  • 401(k) Retirement Savings Plan with competitive employer contributions
  • Competitive paid-time-off programs, including company-paid holidays
  • Competitive Parental Leave Benefits & Adoption Assistance program
  • Employee Assistance Program
  • Tax-Free Commuter Benefit
  • Tuition Reimbursement & Professional Qualification benefits

In today’s world, what do we stand for?

Ethics and integrity are the foundation of delivering on our commitment to you. We believe that core values drive success, and that when relationships are held in the highest regard, there is nothing that cannot be accomplished. At Sompo, our ring is more than a logo, it is a symbol of our promise. Click here to learn more about life at Sompo.

Sompo is an equal opportunity employer and we intentionally value inclusion and diversity. Above all, we want you to work in an environment that respects everyone’s unique contributions – we are passionately committed to equal opportunities. We do not discriminate based on race, color, religion, sex orientation, national origin, or age.

Salary : $100,000 - $170,000

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