A leading specialty insurance organization is seeking a senior underwriting professional to join its casualty underwriting team. This individual will underwrite complex risk management and loss-sensitive accounts while partnering closely with brokers, distribution partners, claims professionals, and internal stakeholders.
This is a high impact individual contributor opportunity for someone who enjoys technical underwriting, relationship management, and portfolio influence without pursuing a traditional people management path.
Responsibilities
Underwrite and manage a portfolio of complex workers compensation and casualty risks
Evaluate loss history, financial statements, operational exposures, and risk characteristics
Structure and negotiate program terms, attachment points, retention levels, collateral requirements, and pricing
Develop and maintain strong relationships with retail and wholesale brokers
Drive profitable growth through disciplined underwriting and portfolio management
Partner with claims, actuarial, and risk management teams on account strategy and performance
Serve as a technical resource and mentor to less experienced underwriters
Monitor market conditions, competitive activity, and emerging industry trends
Maintain underwriting authority and exercise sound judgment on complex submissions
Qualifications
10+ years of commercial underwriting experience with meaningful exposure to workers compensation, casualty, excess casualty, or risk management accounts
Experience underwriting loss-sensitive, self-insured, captive, large deductible, or other structured insurance programs
Strong understanding of attachment points, retention structures, collateral requirements, and pricing methodologies
Demonstrated ability to analyze financials, loss experience, and complex risk exposures
Established broker relationships and strong business development skills
Ability to work independently while collaborating across underwriting, claims, and actuarial teams
Excellent communication, negotiation, and relationship management skills
Preferred Experience
Excess Workers' Compensation
National Accounts
Large Account Casualty
Alternative Risk / Captive Programs
Risk Management Business
Facultative Reinsurance
Employers Liability
Structured Casualty Programs
Preferred Designations
CPCU
ARM or ARM-P
ARe
Why Consider This Opportunity?
Opportunity to underwrite sophisticated and highly structured accounts
Significant autonomy and underwriting authority
Visible role with meaningful influence on portfolio performance
Collaborative and specialized underwriting environment
Hybrid work flexibility
Clear technical leadership path without requiring direct people management
Numbers & Facts
Location
Chicago, IL
Skills
ARM (Advanced RISC Machine)unmatched
Actuarial Skillsunmatched
Brokerageunmatched
Business Developmentunmatched
Communication Skillsunmatched
Competitive Researchunmatched
Distribution Channelunmatched
Financial Analysisunmatched
Financial Operationsunmatched
Financial Statementsunmatched
Industry/Trade Analysisunmatched
Insuranceunmatched
Insurance Underwritingunmatched
Investment Managementunmatched
Market Trackingunmatched
Mentoringunmatched
National Salesunmatched
Negotiation Skillsunmatched
People Managementunmatched
Pricingunmatched
Profit & Loss Analysisunmatched
Reinsuranceunmatched
Relationship Managementunmatched
Retailunmatched
Riskunmatched
Risk Managementunmatched
Sales Managementunmatched
Sales Strategyunmatched
Team Playerunmatched
Technical Leadershipunmatched
Trend Analysisunmatched
Underwritingunmatched
Wholesale Industryunmatched
Worker's Compensationunmatched
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