Remote Regional Surety Leader: Underwriting & Growth

Kalepa; Chicago (IL); Hybrid; USD 110,000 - 160,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability insurance

401(k) match

HSA/FSAs

Job summary

Core Specialty seeks a Commercial Surety Regional Manager in Chicago to lead underwriting for the territory and drive profitable growth. You will manage agency relationships, oversee pricing and terms, and ensure adherence to guidelines while mentoring others.

The role combines market-facing leadership with analytical decision-making, requiring strong communication with brokers, indemnitors, and internal partners. Occasional travel is expected across the region.

Qualifications

• Bachelor’s degree in Business, Accounting, Finance, or related field.
• 5+ years in underwriting roles within the surety industry.
• Strong financial statement analysis and credit underwriting skills.
• Demonstrated success developing agency relationships and generating profitable growth.
• Willingness to travel throughout assigned territory.

Responsibilities

• Lead underwriting for the territory and determine terms and capacity.
• Analyze financial statements and structure indemnity terms.
• Drive profitability and monitor portfolio performance.
• Develop broker and client relationships; collaborate with claims, legal, accounting, and operations.
• Develop underwriters and coach staff; promote best practices and performance.

Skills

Underwriting expertise

Analytical skills

Communication

Software proficiency

Financial analysis

Negotiation

Time management

Independent work

Education

Business/Finance degree

Advanced degree or certs

Tools

Underwriting software

Microsoft Office

Adobe

Job description

Core Specialty seeks a Commercial Surety Regional Manager in Chicago to lead underwriting for the territory and drive profitable growth. You will manage agency relationships, oversee pricing and terms, and ensure adherence to guidelines while mentoring others.

The role combines market-facing leadership with analytical decision-making, requiring strong communication with brokers, indemnitors, and internal partners. Occasional travel is expected across the region.