Underwriter (Houston, Chicago, Boston)

CrossCover; Chicago (IL); On-site; USD 75,000 - 95,000; Full time

Benefits offered by this job

Competitive salary with performance-based incentives

Career growth opportunities

Flexible PTO

Comprehensive benefits (health, dental, vision)

Job summary

A leading commercial property insurance firm is seeking an experienced Property Underwriter in Chicago. In this role, you will assess insurance applications, analyze risks, and manage a book of business. Successful candidates will bring 5-10 years of underwriting experience and strong analytical skills. The firm offers competitive salaries, flexible PTO, and comprehensive benefits. Join us to make an impact in the commercial property insurance sector!

Qualifications

• 5-10 years of experience in underwriting and risk assessment.
• Strong analytical and critical-thinking skills.
• Deep understanding of commercial insurance.

Responsibilities

• Underwrite and analyze new and renewal commercial property accounts.
• Manage and maintain an existing book of business.
• Work closely with broker partners.
• Ensure underwriting decisions align with company guidelines.

Skills

Analytical skills

Negotiation skills

Communication skills

Attention to detail

Collaboration

Tools

Underwriting software

Job description

About the Role:

We are seeking an experienced Property Underwriter to join our growing open market team focused on middle-market risks. In this role, you will assess and evaluate insurance applications, analyze risk factors, and determine coverage terms in line with CrossCover’s underwriting guidelines and authority. You’ll work closely with brokers, and internal teams to build and maintain strong relationships while driving profitable growth.

Who We Are:

CrossCover is an E&S Commercial Property MGU based in Cypress, Texas, specializing in reducing reinsurance costs and minimizing volatility from catastrophes (CAT) for our carrier partners. We strategically leverage our CAT capacity to write non-CAT risks across the country. Our team thrives on working in a fast paced environment exceptional service and customized solutions—and we reward results.

What You’ll Do:

• Underwrite and analyze new and renewal commercial property accounts

• Manage and maintain an existing book of business

• Work closely with broker partners

• Ensure underwriting decisions align with company guidelines and risk appetite

What You’ll Need:

• 5-10 years of experience in underwriting and risk assessment

• Strong analytical and critical-thinking skills

• Deep understanding of the commercial insurance landscape

• Excellent attention to detail and organizational skills

• Strong negotiation and communication skills (written & verbal)

• Ability to collaborate effectively in a fast-paced environment

• Proficiency in underwriting software and tools

• Professional certifications (CPCU, ARM) are a plus

What We Offer:

• Competitive salary with performance-based incentives

• Career growth and advancement opportunities

• Flexible PTO/Discretionary Time Off

• Comprehensive benefits: health, dental, vision, disability, life insurance, 401(k), and more

Join us and be part of a team that’s reshaping the commercial property insurance landscape!