Underwriting Supervisor - Transportation

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.

We’re growing at West Bend! Our Commercial Lines Underwriting team is central to driving profitable growth.This is a working supervisor role where you’ll have the unique opportunity to build your team from the ground up. You’ll lead by example—balancing strategic oversight with hands-on underwriting responsibilities—while shaping a high-performing team focused on transportation risks.

This position offers a hybrid work schedule. Candidates who are located within 50 miles of a West Bend office location will work a hybrid schedule for collaboration days, team meetings or other in-person events. The position can be based in West Bend, Madison or Appleton.

The internal deadline to apply is 10/01/2025. External applications will be accepted on a rolling basis while the position remains open.

• Develop and continually improve the underwriting quality and marketing talents or staff support quality for an assigned group of Underwriters and Assistant Underwriters.
• For line underwriting, techniques for accomplishing this goal include formal and informal referral situations, individual file reviews and re-underwriting projects.
• Responsible for the selection and training of new associates in the department, as well as all supervisory activity for their assigned group; including performance management, salary administration, career development plans, etc.
• Will complete special projects and other duties as assigned by the Underwriting Manager.

Preferred Experience and Skills

• 7 years of experience in commercial transportation underwriting
• Leadership skills, with the ability to coach, mentor and develop others
• Analytical and communication 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 $106,451-$133,064.

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.