Assistant Underwriter-Surety

The Silver Lining; Madison (WI); Hybrid; USD 62,000 - 77,000; Full time

Benefits offered by this job

Medical & Prescription Insurance

Health Savings Account

Dental Insurance

Vision Insurance

Short and Long Term Disability

Flexible Spending Accounts

401(k) Plan with Company Match

Paid Time Off

Bonus eligible based on performance

Job summary

West Bend is seeking a trainee underwriter in a hybrid role based near Madison/West Bend. You will learn underwriting principles, support agency partners, and gain hands-on experience through mentorship and real-world assignments.

The role emphasizes independent work, data analysis, and strong communication within a high-performance team. Expect collaboration days, training, and opportunities for career growth within a respected insurer.

Qualifications

• Bachelor’s degree in business, insurance, or related field.
• 0-1 years of experience in the surety industry preferred.
• Strong communication and analytical skills.

Responsibilities

• Learn underwriting principles through instructor-led training, testing, and mentoring.
• Support underwriting needs, business processing, and service goals for producers.
• Assist with underwriting file maintenance and refer new/existing business to a senior underwriter.
• Develop and maintain agency/broker relationships for positive outcomes.
• May travel regionally to agency locations, shadowing senior underwriters.
• Communicate effectively with agents and provide prompt, quality service.
• Represent the company at agency/industry functions.
• Promote and uphold division and company values.

Skills

Underwriting basics

Independent work

Data analysis

Multitasking

Communication skills

Team collaboration

Education

Bachelor’s degree in business/insurance

Job description

Company Overview

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.

Job Summary

The internal deadline to apply is 10/30/2026. External applications will be accepted on a rolling basis while the position remains open.

Start your career in surety underwriting with hands-on training, mentorship, and real-world experience. In this role, you'll support underwriting activities, analyze business opportunities, build relationships with agency partners, and deliver quality service while developing the skills needed for a successful underwriting career.

Work Location

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 Madison, WI.

Responsibilities & Qualifications

Summary of Responsibilities

Responsible for learning underwriting principles and standards through instructor led training, testing, self-study courses, and practical application with guidance through a formal mentoring program. Works with the team to support underwriter needs, business processing, and service goals for our producer partners. Assists with underwriting file maintenance, and analyzes, evaluates, and refers new and existing business to a senior regional underwriter. May also have limited authority to assist with the underwriting and servicing of smaller business opportunities. Develops and maintains agency and/or broker relationships to ensure positive outcomes. May occasionally travel within the region to agency or principal locations, shadowing senior underwriters prospecting business. Communicates effectively with agents and provides prompt, quality service. May represent the company at agency and industry related functions. Promotes and complies with the values of the division and company.

Preferred Experience and Skills

• 0-1 years of experience in the surety industry
• Ability to work independently and perform quality work within deadlines.
• Data entry and analytical skills
• Ability to multi-task
• Effective communication skills in all mediums including phone, e-mail, and in-person.
• Ability to interact professionally and work well in a high-performance team environment.

Preferred Education and Training

• Bachelor’s degree in business, insurance, or related field

Salary Statement

The salary range for this position is $61,549 - $76,936The 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.

Benefits

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.

EEO

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.