Sentry Insurance Logo Territory Executive-National Accounts (WC Loss Sensitive)

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As the Territory Executive for Sentry in our National Accounts division, you’ll work with brokers and agents in a defined territory to create Sentry awareness.

You will be responsible for generating new business submissions and working with the team to create and sell Workers Compensation new business proposals. You’ll be the team leader in the sales of loss sensitive casualty business to National Account Workers Compensation clients with large commercial account premiums

What You’ll Do

The Territory Executive-National Accounts will be responsible for broker and client relationships in North Carolina, South Carolina, West Virginia, Virginia, and Tennessee. The ideal candidate will reside in the territory or in Stevens Point, WI and will be required to travel regularly to meet with brokers, clients, and prospects.

You will work closely with our Underwriting personnel in order to obtain/retain large individual commercial Workers Compensation accounts. Additionally, you’ll:

  • Solicit accounts through selected brokers or in response to inquiries from prospective clients.

  • Work with Underwriting, Loss Control, and Claims to determine acceptability of the risk and services needed.

  • Serve as the primary contact with assigned accounts and their brokers.

  • Collaborate with the appropriate functional units to provide exceptional service to your accounts.

  • Deliver and present proposals to brokers and prospective clients and discuss Sentry advantages and differentiators.

  • Daily engagement with Microsoft Dynamics CRM

What it Takes

In order to be eligible for this elite opportunity you must meet the following criteria:

  • Bachelor’s degree or equivalent work experience with National Accounts Workers Compensation Casualty business.  Experience with Sales and Underwriting of large Risk Management type accounts is preferred.

  • 5-8 years of experience with an insurance carrier, commercial agency or brokerage preferred.

  • Current or prior broker/agent relationship experience preferred

  • Previous technical insurance experience, preferably in sales and/or underwriting.

  • Highly motivated self-starter with the drive to be a top performer.

  • Exceptional communication, organization and selling skills.

  • Ability to travel extensively (5-7 nights per month) and have a valid driver’s license and ability to have and maintain an acceptable motor vehicle report.

  • Required to have primary residence within your sales territory or be located near our office location in Stevens Point, WI.

What You’ll Receive

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

  • Competitive Salary with significant bonus potential

  • Company car and 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!

Casey Van Der Geest

Casey.VanDerGeest@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.

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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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Job Data

Company: Sentry Insurance

Location: Nashville, TN

Posted: May 28, 2026

Category: Sales