Territory Underwriting Specialist

Sentry Insurance
Boston, MA

Markets companies' products and services to assigned Commercial Lines accounts and independent agencies.

The ideal candidate for this position will be located in the state of Massachusetts, with travel required in and around that area.



What You'll Do:

The Territory Underwriter Specialist will be responsible for agent and broker relationships. In addition, you will...

  • Solicit accounts through select agents and brokers

  • Evaluate, underwrite, and price prospective accounts to select independent agents

  • 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 :

  • Bachelor’s degree or equivalent work experience

  • Minimum of 5 years related work experience, with multi-line middle market underwriting experience handling accounts in construction, manufacturing, wholesale, real estate, and service industries preferred

  • Previous technical insurance experience, preferably with sales

  • Experience with underwriting large complex accounts

  • Exceptional communication and relationship building skills

  • Strong business and pipeline development skills

  • Ability to meet travel requirements as you’ll be prospecting new business opportunities in an agent office; meeting with insureds during safety inspections, and participating in mid-year claims review meetings

  • Ability to travel and have a valid driver’s license with the ability to maintain an acceptable motor vehicle record

What You'll Receive :

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

  • Company car with gas card.

  • 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 Massachusetts, the range for annual compensation, based on qualifications and experience is between $132,700 - $199,100

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. 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

Talent Acquisition Specialist Senior

[email protected]

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.

Posted 2026-04-09

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