Jobs › Sentry Insurance

Underwriting Manager - Middle Market

Sentry Insurance · Madison, WI · Full time

Posted Aug 27, 2026 · We last checked this listing on Oct 6, 2026

Apply at Sentry Insurance

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you coached an underwriter whose files kept getting sent back.

What they are checking: Whether they develop people through specific feedback instead of just fixing the work themselves.

Tell me about a time you worked with other teams to win a new account.

What they are checking: Whether they collaborate across functions and present well in new-business pursuits.

Tell me about a time you had to have a hard performance conversation. What happened afterward?

What they are checking: Whether they address performance directly and fairly instead of avoiding it.

What would you do

How do you balance growth and profitability when an agency is pushing hard on a large account with mixed loss history?

What they are checking: Whether they can protect underwriting discipline while keeping an important agency relationship healthy.

You think a process is slowing the team down. How would you change it and know whether the change worked?

What they are checking: Whether they improve processes and then check results, which the posting asks them to monitor.

An insured calls you directly, angry about a declined renewal. How do you handle it?

What they are checking: Whether they can handle difficult inquiries personally while backing a sound decision.

This role is in our Madison regional office on a hybrid model. How do you lead a team when people aren't always in the office together?

What they are checking: Whether they can keep a hybrid team connected and consistent in how they underwrite.

About the work

Walk me through how you'd review a complex middle market account that's beyond your underwriters' authority.

What they are checking: Whether they have the technical depth to interpret guidelines on the hardest files the team sees.

What metrics do you watch to know whether your team's book is healthy?

What they are checking: Whether they manage with real measures like loss ratio, retention, hit ratio and rate, not gut feel.

What lines of coverage in middle market do you know best, and where are you less sure?

What they are checking: Whether they have an honest view of their technical range across all middle market lines.

How do you design underwriting training for a mix of new and experienced underwriters?

What they are checking: Whether they can build training that meets people at different levels rather than one-size-fits-all.

Practice this interview out loud.

Offer builds a real interview for this exact role at Sentry Insurance from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Sentry Insurance.

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 Here is what you can look forward to as part of our team: At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally. • Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one. • Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled. • Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program. • Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available. • Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community. • Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately. • Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities. Why Join Sentry? At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads , as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity . These honors reflect our commitment to your professional satisfaction and growth. Building on a Legacy Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years. Your Career, Our Community Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth. Ready to own your future? Join us at Sentry, opportunities await! Joe Larsen 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.

Apply at Sentry Insurance