Underwriting Manager - Middle Market

Sentry Insurance; United States; Hybrid; USD 110,000 - 150,000; Full time

Benefits offered by this job

Hybrid work model

Equipment for home office (laptop)

Meal Subsidy

401(k) with company match

Sentry University (SentryU) andTuition

Generous Paid Time Off

Health, Dental, Vision, Life insurance

Parental leave

Well-being and Employee Assistance

Sentry Foundation gift matching

Job summary

Sentry Insurance in Madison, WI, is seeking an Underwriting Manager - Commercial Lines to lead a team of underwriters and drive our mid-market strategy. This role combines strategic oversight with hands-on guidance to ensure productivity, profitability, and policy quality across complex files.

The ideal candidate has a bachelor’s degree, at least two years in middle market underwriting, and relevant insurance coursework (IIA/CPCU).

Qualifications

• Bachelor’s degree or equivalent work experience.
• Minimum 2 years in middle market underwriting;
• Strong analytical, communication, and interpersonal skills.

Responsibilities

• Oversee day-to-day underwriting operations and guide a team of underwriters.
• Implement changes to improve productivity, growth, profitability, and quality.
• Interpret underwriting guidelines for larger or more complex files.
• Coordinate underwriting training programs.
• Develop and maintain relationships with agencies and insureds.

Skills

Analytical skills

Communication skills

Leadership

Team management

Travel flexibility

Education

Bachelor's degree or equivalent

CPCU or insurance courses

Management coursework

Job description

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.
• 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.
• 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 [e-mail]

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. Our associates are the most important part of our company. We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses. We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company. Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.