Underwriting Supervisor - West Bend Express

Recognized as a Milwaukee Journal Sentinel Top Workplace for 14 consecutive years, including three years of being honored as number one! Join us at West Bend, where we believe that our associates are our greatest asset. We hire talented individuals who are conscientious, dedicated, customer focused, and able to build lasting relationships. We create and maintain an environment where you feel a sense of belonging and appreciation. Your diversity of thought, experience, and knowledge are valued. We’re committed to fostering a welcoming culture, offering you opportunities for meaningful work and professional growth. More than a workplace, we celebrate our successes and take pride in serving our communities.

The Underwriting Supervisor provides day‑to‑day leadership for an assigned group of Underwriters, ensuring underwriting quality, consistency, and productivity. This role focuses on coaching, performance oversight, including those who are newer to the underwriting position, execution of underwriting initiatives, and continuous improvement while serving as a key connection between Underwriting associates and leadership.

The internal deadline to apply is 11/11/2026. External applications will be accepted on a rolling basis while the position remains open.

This position offers a hybrid work schedule of 2 days remote and 3 days onsite per week out of the West Bend or Madison, WI offices. 

Summary of Responsibilities

The Underwriting Supervisor provides day‑to‑day leadership for an assigned group of Underwriters, ensuring underwriting quality, consistency, and productivity. This role focuses on coaching, performance oversight, execution of underwriting initiatives, and continuous improvement while serving as a key connection between Underwriting associates and leadership.

Key Responsibilities

• Provide day‑to‑day supervisory leadership for an assigned team of Underwriters, with accountability for underwriting quality, consistency, and productivity.
• Support Underwriting associates through coaching, file reviews, referral guidance, and ongoing performance feedback to ensure adherence to underwriting guidelines and operational expectations.
• Execute underwriting initiatives, process changes, and workflow updates as directed by leadership; monitor adoption, effectiveness, and results.
• Review underwriting and operational performance data to identify trends, risks, and development opportunities; communicate insights and recommendations to leadership.
• Support learning and development of new Underwriting associates to ensure successful integration and skill development.
• Foster and participate in special projects and continuous improvement efforts aimed at enhancing underwriting processes, efficiency, and outcomes.
• Serve as an escalation point for underwriting questions and complex referrals, providing guidance consistent with established authority and guidelines.

Preferred Experience and Skills

• 7 years of experience in commercial multi-line underwriting.
• Prior leadership, supervisory, or lead experience preferred.
• Coaching, feedback, and performance management skills.
• Ability to manage multiple priorities in a fast‑paced underwriting environment while maintaining attention to detail and quality.
• Ability to analyze data, identify trends, and translate insights into action.
• Effective communication and organizational skills.

Preferred Education and Training

• Bachelor’s degree in Business, Insurance or related field
• Completion of Associate in Underwriting program and CPCU designation

The salary range for this position is $109,432 - $136,790

The actual base pay offered to the successful candidate will be based on multiple factors, including but not limited to job-related knowledge/skills, experience, business needs, geographical location, and internal equity.  Compensation decisions are made by West Bend and are dependent upon the facts and circumstances of each position and candidate.  

West Bend offers a comprehensive benefit plan including but not limited to:   

• Medical & Prescription Insurance  

• Health Savings Account  

• Dental Insurance  

• Vision Insurance  

• Short and Long Term Disability  

• Flexible Spending Accounts  

• Life and Accidental Death & Disability   

• Accident and Critical Illness Insurance  

• Employee Assistance Program  

• 401(k) Plan with Company Match  

• Pet Insurance  

• Paid Time Off. Standard first year PTO is 17 days, pro-rated based on month of hire. Enhanced PTO may be available for experienced candidates 

• Bonus eligible based on performance  

• West Bend will comply with any applicable state and local laws regarding employee leave benefits, including, but not limited to providing time off pursuant to the Colorado Healthy Families and Workplaces Act for Colorado employees, in accordance with its plans and policies.

West Bend provides equal employment opportunities to all associates and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, and promotion.