Middle Market Underwriter

At Sentry, we understand that underwriting is more than just assessing risk—it's about building trusted relationships and delivering thoughtful insurance solutions.

We're looking for an experienced Middle Market Underwriter to join our Regional team. If you thrive on analyzing complex risks, collaborating with independent agents, and growing profitable commercial books of business, this opportunity is for you.

As a Territory Underwriter Specialist or Underwriter Specialist Senior (depending on your qualifications), you’ll play a vital role in driving business results by:

• Marketing and underwriting commercial property and casualty products across construction, manufacturing, real estate, service, and wholesale industries.

• Managing a diverse book of middle market business and fostering relationships with select independent agents and brokers.

• Leading prospecting efforts, evaluating new agencies, and helping shape Sentry’s presence in the Ohio region.

• Collaborating with teams across underwriting, claims, and loss control to deliver smart, comprehensive service to our customers.

Our team-focused approach to underwriting and servicing accounts will help you develop an insurance program specifically designed for each customer—whether their exposures apply to property, general liability, auto, workers’ compensation, or other essential coverages.

With a variety of deductible options, liability limits, and payment plans, you can build a package that helps keep your clients protected from the risks their businesses face every day.

With more than 120 years serving businesses of all sizes, Sentry is part of one of the largest and most financially secure mutual insurance groups in the U.S., with $27.5 billion in assets, an $8 billion surplus, and an A+ (superior) rating from AM Best, the industry’s leading rating authority, for 34 consecutive years.*

Our commitment to our associates, agents, and customers sets us apart—and we’re proud to deliver commercial insurance with confidence, clarity, and care.

If you’re ready to use your experience and skills to shape lasting relationships and strengthen business insurance strategies, we want to hear from you. Learn more about this position and the benefits you’ll receive—and submit your application.

Apply now.

We look forward to hearing from you.

*Assets and policyholder surplus are as of December 31, 2024, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. A+ (superior) AM Best Financial Strength Rating (FSR) current as of June 2025. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.