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Territory Underwriting Specialist


Sentry’s dedication to customers is embodied by our best employees.  At Sentry, our associates take care of our customers with a passion for service and deliver business results.  We are currently seeking an experienced, self motivated and results driven individual to fulfill a highly skilled position as a Territory Underwriter Specialist.. As a Territory Underwriter Specialist for our Northeast Regional operation, you’ll market Sentry’s products and services to assigned Commercial Lines accounts, independent agents and brokers in a defined territory.  You will manage and coordinate the sales and placement of middle market business with premium sizes up to $500K in a wide variety of classes and lines of business.

What You'll Do

The Territory Underwriter Specialist will be responsible for agent and broker relationships.  The ideal candidate for this position will reside in Northeastern MA, Southern  NH or Southern ME. In addition you’ll:
• Solicit accounts through selected agents and brokers
• Evaluate prospective accounts and independent agencies to determine acceptability of risk
• Serve as the primary contact with assigned agents and brokers
• Provide comprehensive sales expertise to increase production through agency channels
• Work with assigned agents and brokers on the coordinating of resolutions

What it Takes

• Bachelors Degree and equivalent work experience with property and casualty business
• 5-8 years of experience with an insurance carrier, commercial agency or brokerage (underwriting 7+ yrs)
• Previous technical insurance experience, preferably with sales
• Past experience with underwriting large complex accounts
• Highly motivated self starter with the drive to be a top performer
• Exceptional communication, organization and selling skills
• Strong business and pipeline development skills
• Ability to travel and have a valid driver’s license with the ability to maintain an acceptable motor vehicle record.
• Ability to travel 25% of the time.


What You'll Receive

There is a reason why Sentry made Forbes’ list of America’s Best Midsize Employers in 2017 and 2018. At Sentry, we recognize there are many factors that contribute to your overall satisfaction both at work, and in your personal life. So, we provide a perfect mixture of compensation, benefits, company culture, and resources to ensure your everyday happiness. Below are some benefits that you’ll receive.

  • Competitive compensation to reward you for your hard work every day.
  • Generous Paid-Time Off Plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help fund your future. 
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Volunteer Time Off so you can dedicate time to the community.
  • Sentry Foundation gift matching program to encourage charitable giving.

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please upload your resume directly, in addition to completing your online application details.

Who You’ll Want to Contact

Jeff Endres at 608/826-3316

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service 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.


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.


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

Equal Employment Opportunity

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.


Job Title:
Territory Underwriting Specialist
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