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Dairyland Inbound Sales Representative


Sentry Insurance is seeking a highly motivated, self-starter with strong organizational skills to join our team of insurance agents. This team focuses on incoming sales calls for our Motorcycle and Non-Standard Auto written through Dairyland Insurance. 

Our call center is open from Monday through Friday, 7am-9pm CST, and Saturdays from 8am – 6pm CST.  As an insurance agent, your flexibility to work within these hours is a key factor to the department’s success. Hours for current position are between 11:15am to 9:05pm CST and are subject to change based on business need and individual performance.  

Take the sales skills you have acquired over the years to the next level or make a change and start down your new career path today with our team of professionals at one of the largest mutual insurance companies in the U.S.  New Hires coming to us with an active PL or P&C License will receive a $2000 Sign-on Bonus after all non-resident licenses and appointment have been obtained.

What You'll Do


As an insurance agent, you will be responsible for selling Dairyland products to meet growth, retention, profit and sales objectives within our Motorcycle and Non-Standard Auto business units.

•    Promote Dairyland Insurance Services product and services to customers.
•    Understanding of specific company products. 
•    Answer inbound customer inquiries on coverage limits, deductibles, etc.
•    Provide quotes and bind coverage for customers in a timely fashion.

What it Takes


•    Associate Degree or equivalent work experience.
•    Bilingual fluency in English/Spanish is strongly preferred. 
•    Effective phone communication, analytical, decision making, and human relation skills.
•    Previous call center experience required. 
•    Effective multi-tasking and time management skills.
•    Property & Casualty or Personal Lines license is strongly preferred.
•    Proficient computer skills with the ability to use dual monitors.  
•    Ability to work non-traditional hours, including evenings and weekends.


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 between hourly wage, monthly and annual bonus incentives.  Bonus potential based on individual sales performance.
  • Shift differential of 10% for weekday hours after 5pm and weekend hours.
  • Carpool incentives.
  • Health incentives for gym.
  • Group Medical, Dental, Vision and Life benefits.
  • Generous Paid Time Off - including applicable company holidays.
  • 401k plan with a dollar-for-dollar match on your first 8% – with immediate vesting.
  • Access to more than 100 company paid certifications, designations, and licensing courses. 
  • Career advancement opportunities.
  • Volunteer opportunities.

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

Kacie Akey

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:
Dairyland Inbound Sales Representative
Job ID:
Freeport, IL
Full/Part Time:

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