You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.
We provide everything you need to carve out a sales career filled with success and purpose, including:
High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips
Outstanding benefits and a 401(k)-program matching dollar for dollar up to 8%
Opportunities for professional development and growth
Outstanding training and support
An industry-leading line of products and services
Total currently estimated projected compensation range for this position is $62,442-$98,442, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities – both renewal and new business -- are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.
The North Dakota territory includes: All of North Dakota and Northwestern Minnesota. Residence within the sales territory is required.
What You’ll Do
Sell directly to niche market accounts to increase premium volume
Retain profitable business by providing effective, quality service to policyholders
Build and maintain quality relationships with businesses
Work directly with Underwriting, Claims, Loss Control, Audit, Customer Service, and other key partners
Call on and pursue all niche market opportunities assigned to your geographic territory
Leverage current customers and relationships for new growth and sales opportunities
What it Takes
Bachelor’s degree or equivalent work experience/related sales experience
The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers
Self-discipline and ability to thrive in a remote work environment
Ability to multitask, prioritize, communicate effectively, and remain organized
Strong analytical and math skills
Acceptable Motor Vehicle Record with a valid driver’s license and ability to meet travel requirements
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
Home Office: Enjoy the best of both worlds. With a home office set up and time in the field, with regular travel in your company car in your defined territory. We provide the cutting edge proprietary technology and tools you need to be more efficient and effective in the field including a laptop and cell phone reimbursement.
Continuous Learning: Unlock your potential through Sentry University, including comprehensive, ongoing training, including licensure and take advantage of our tuition reimbursement program.
Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
Why Join Sentry?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
Building on a Legacy
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
Your Career, Our Community
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us at Sentry, opportunities await!
Kristina Forbes
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.
Skills Required
- Residence within the sales territory
- Bachelor's degree or equivalent work experience/related sales experience
- Ability to obtain and maintain required P&C and Life insurance licenses
- Acceptable Motor Vehicle Record and valid driver's license
- Ability to meet travel requirements (territory-based travel)
- Self-discipline and ability to thrive in a remote work environment
- Ability to multitask, prioritize, communicate effectively, and remain organized
- Strong analytical and math skills
What We Do
Your business. Your employees. Your peace of mind. At Sentry, we understand what matters most to you. Because we’ve been there ourselves. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. Establishing the company gave members strength in numbers, but it was the true strength of personalized service and Midwestern roots that became hallmarks of the Sentry name. Today, we’ve grown to become a member of one of the largest and most financially secure insurance groups in the country by never forgetting where we came from. Perhaps that’s why many of our customers have been with us for decades. And we can be there for you. Our customers work in a wide range of industries, including transportation, manufacturing, metalworking, construction, auto dealerships, and more. From 401(k) plans and general liability to commercial property and workers’ compensation, we offer the insurance products that can help protect your business and your employees. Our Stevens Point headquarters is the flagship of our business, which is supported by field offices strategically located throughout the United States. With more than $22.9 billion in assets, a $7.5 billion* policyholder surplus, and an A+ (superior) rating from AM Best,** the industry’s leading rating authority, we continue providing peace of mind. One conversation at a time. To learn more about us, the industries we serve, and the products we offer, visit sentry.com. The content provided here is for informational purposes only: https://www.sentry.com/footer/legal-disclaimer. *Assets and policyholder surplus are as of December 31, 2022, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. **Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2023. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.

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