Territory Underwriter Specialist

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As a Territory Underwriter Specialist, you’ll market & underwrite Sentry’s products & services to select Commercial Lines independent agents & brokers in a defined territory.

We are currently seeking an experienced, self-motivated and results driven individual to fulfill a highly skilled position as a Territory Underwriter Specialist. You will manage and coordinate the sales and placement of middle market business 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 would reside in Northern California.

In addition, you’ll:

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
Knowledge of the Northern California marketplace, and existing or past relationships with larger independent agents 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

Based on experience and qualifications, the pay range for this position is: $144,720-$217,200 annually.

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.

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

Joe.Larsen@Sentry.com

Talent Acquisition Specialist Senior

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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