Insurance Underwriter Assistant Jobs in Milwaukee, WI

Recognized as aMilwaukee Journal SentinelTop 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 are growing at West Bend! Our Commercial Lines Underwriting team plays a critical role in our journey towards profitable growth. Our Underwriters are relationship focused with strong communication skills, motivated, and work in a fast-paced team environment. West Bend is an industry leading carrier that works solely through the independent agency system. We are looking for a highly experienced Transportation Underwriter to join our dynamic team!

This position offers both remote and hybrid work locations. Candidates who reside within 50 miles of an office location (West Bend, Madison, Appleton) will be offered a hybrid work schedule. Candidates who are fully remote (beyond 50 miles) may occasionally be asked to travel to an office location for in-person engagement activities such as team meetings, training and corporate events.  

The internal deadline to apply is 8/14/26. 

• Meet agency profitability and production objectives for an assigned group of agencies by underwriting new commercial business, renewal policies and policy endorsements.
• Understand and evaluate exposures related to individual risks through continued mentoring involvement.
• Integrate these functions within the workflow of a Commercial Underwriter.
• Assist in the analysis of individual agency and book of business results to determine if any corrective actions are needed.
• Support the Commercial Enterprise Division and the Regional Sales Manager in identifying corrective measures needed to assure an underwriting profit.
• Help in establishing specific action plans where needed and assist in communicating these effectively with agents.
• Assist the Regional Sales Manager in developing written premium goals at an agency and book of business level.
• Support achievement of these goals by promoting the benefits of our product line to agencies by personal visits, regular telephone contact and appropriate promotional mailings.
• Provide territory performance reports and action plans to leadership as needed.
• Participate in agency meetings, events and with loss control representatives during service calls and prospect service.
• Participate and/or lead practice group, coordinate and document meetings.
• May maintain and develop customized reports for loss control representatives to share with accounts.  Communicate effectively with agencies in the development of underwriting and exposure information and supports attainment of written premium goals by providing exceptional service.
• Act as a source of reference for underwriting support staff, assistant underwriters, associate underwriters and others.
• Provide guidance and mentoring support to underwriter I and/or II as needed.

Preferred Experience and Skills

•  Five years of experience in commercial transportation underwriting
•  Analytical skills and attention to detail
• Oral and written communication skills
• Organizational skills
•  Interpersonal skills
• Mentoring skills

Preferred Education and Training

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

The salary range for this position is $75,101-$93,876.

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.

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