Underwriting Manager - Middle Market

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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 Denver, CO 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.
In the state of CO, the annual compensation for this position, based on qualifications and experience is between $145,900 - $218,900.

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.

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5 Questions You Should Ask During the Interview

Here are 5 questions we think you could ask during your interview. Use them as a guide to help you write your own questions.

Remember: Always have at least 5 questions prepared for the interview. If you do not, you run the risk of looking unprepared.

What does success look like in this role, and how is it measured?

Why ask this? You want to ensure you have a clear understanding of expectations before accepting the role. Knowing how success is measured helps you hit the ground running and avoid surprises about performance evaluations. It also signals to the employer that you're results-driven.

Can you describe the team dynamic and the company culture?

Why ask this? Skills and experience matter, but if the work environment isn’t a good fit, you won’t be happy or productive. This question helps you gauge whether the company values collaboration, how teams interact, and whether the culture aligns with your work style and values.

What are the biggest challenges facing the person in this role right now?

Why ask this? Every job has challenges, and it’s better to know them upfront. This helps you assess whether the role is a good fit for your strengths and whether the company is realistic about its expectations. If they hesitate to answer, it could be a red flag.

How does the company support work-life balance and employee well-being??

Why ask this? Burnout is real, and some companies expect employees to sacrifice personal time for the job. By asking this, you’ll get a sense of how they value work-life balance, flexibility, and well-being—things that are crucial for job satisfaction and long-term success.

These questions help you make an informed decision while also showing your professionalism and strategic thinking!

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