Underwriting Supervisor – Workers Comp

Jobtailor; West Bend (WI); On-site; USD 90,000 - 120,000; Full time

Job summary

Jobtailor in Wisconsin seeks an experienced Underwriting Manager to lead a geographic underwriting operation, supervising Supervisors, Underwriters, and Assistant Underwriters.

You will foster agency relationships in the assigned territory, oversee risk acceptance and pricing, and mentor teammates to improve performance and profitability. This role requires strong leadership, analytical skills, and travel readiness.

Qualifications

• 8+ years in property/casualty insurance.
• 3+ years in a leadership role.
• Strong mentoring and development abilities.
• Experienced in risk assessment and pricing strategies.

Responsibilities

• Manage a geographic underwriting operation with Supervisors and Underwriters.
• Foster agency relationships in the assigned territory through in-person travel.
• Oversee acceptance, declination, and pricing of risks.
• Counsel and mentor underwriters on complex risks.
• Review decisions for risks beyond authority.
• Drive profitable growth and performance of the book.
• Recommend underwriting guidelines and pricing adjustments.
• Train and mentor associates and manage personnel actions.

Skills

Leadership

Mentoring

Analytical thinking

Communication

Organizational skills

Education

Bachelor's degree in Business, Insurance, or related field

CPCU designation preferred

Job description

• Manage a geographic underwriting operation, including Supervisors, Underwriters, and Assistant Underwriters
• Foster agency relationships in the assigned territory through in-person travel
• Oversee acceptance, declination, and pricing of risks
• Counsel and mentor Underwriters on complicated risks
• Review underwriting decisions for risks exceeding Underwriters’ authority
• Drive profitable growth and performance of the book of business
• Recommend or implement underwriting guidelines and pricing adjustments when appropriate
• Train and mentor associates
• Initiate personnel actions including salary adjustments, performance evaluations, and promotions

Requirements

• At least 8 years of professional experience in the property/casualty insurance industry
• At least 3 years of experience in a leadership role
• Leadership skills and ability to mentor and develop others
• Analytical, organizational, planning, and communication skills
• Valid driver’s license
• Bachelor’s degree in Business, Insurance, or a related field
• CPCU designation preferred

Core Competencies

Demonstrates extensive experience in managing underwriting operations within the property/casualty insurance industry, with a strong focus on leadership, mentorship, and analytical decision‑making. Proven ability to foster agency relationships and drive profitable growth through effective risk assessment and pricing strategies.

Hard Skills

• Underwriting Guidelines
• Risk Pricing
• Analytical Skills
• Organizational Skills
• Planning Skills

Soft Skills

• Mentoring
• Communication Skills

Certifications & Qualifications

• CPCU Designation

Industry Keywords

• Property/Casualty Insurance
• Underwriter
• Assistant Underwriter
• Supervisors
• Performance Evaluations