Demo

Underwriting Manager - Middle Market

Sentryinsurance
Madison, WI Full Time
POSTED ON 8/10/2026
AVAILABLE BEFORE 9/8/2026
Manages a group of associates who have underwriting responsibility for all middle market lines, responsibly growing strategy, talent, and business.

This position will be located in our Madison, WI Regional office under a hybrid work model.

What You'll Do:

As an Underwriting Manager - Commercial Lines, you will oversee and guide the implementation and successful execution of our business strategy and uphold continuous improvement through leadership focused on process, problem solving, performance, partnering, purpose and people. In addition, you will:

  • Manage the day-to-day underwriting operations while providing technical guidance to a team of underwriters.

  • Recommend and implement changes to improve productivity, growth, profitability, and quality, as well as monitor effectiveness of these policies and procedures.

  • Interpret underwriting guidelines for larger or more complex files.

  • Handle difficult underwriting inquiries through direct personal action.

  • Coordinate and participate in underwriting training programs

  • Attend cross functional team meetings, present and work with other teams in pursuing new accounts, as well as agencies/insureds to develop and maintain effective business relationships.

What it Takes:

  • Bachelor's degree or equivalent work experience

  • Minimum 2 years of related work experience, with experience in middle market underwriting preferred

  • Completion of insurance courses such as IIA and CPCU preferred

  • Previous courses in management or management experience preferred

  • Thorough knowledge of specific insurance concepts and terminology

  • Effective analytical, human relations and communications skills

  • Ability to meet travel requirements of the job

What You'll Receive:

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll receive.

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday in office. As a Sentry associate, you will have an in-office workspace and materials for your home office.

  • In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.

  • Meal Subsidy available for associates who report to an office.

  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.

  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program

  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off

  • Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.

  • Well-being and Employee Assistance programs

  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry:

We take great pride in making Forbes' list of America's Best Midsize Employers since 2017. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Joe Larsen

Senior Talent Acquisition Specialist

Joe.larsen@sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Salary.com Estimation for Underwriting Manager - Middle Market in Madison, WI
$131,270 to $171,567
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