Licensed Direct Sales Representative - P&C (Freeport)

Sentry Insurance
Freeport, IL
Responsible for selling and servicing Sentry products to meet growth, retention, profit and sales objectives for Non-Standard Auto and Personal Lines.

This position will be located in either our Stevens Point, WI, Goldsboro, NC, Freeport, IL, or El Paso, TX Office, or has the potential to work remotely from home. Based on qualifications and experience, this position can be filled at either a Direct Sales Agent - Personal Lines I or Direct Sales Agent - Personal Lines II level.

What You'll Do:

As a Personal Lines Sales Agent, you will be responsible for:

  • Selling Dairyland and Harley Davidson products to meet growth, retention, profit and sales objectives within our business units.

  • Promote Dairyland and Harley Davidson 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:

  • Associates degree or equivalent work experience

  • 6+ months of related work experience

  • Property & Casualty or Personal Lines license is required.

  • Background in technical insurance (rates, coverage, customer service, and/or insurance environment) beneficial; sales experience preferred

  • Communication, analytical, decision making, and human relation skills to deal effectively with prospects and customer issues in a professional manner

  • Effective listening skills and the ability to oidentify the specific nature of the inquiry

  • Effective muti-tasking and time management skills

  • Proficiency of MS office products (Outlook, Word, Excel) internet, and other related computer applications

  • Ability to obtain and maintain required state licensing and carrier appointments

  • Bilingual fluency in English/Spanish a plus, but not required

  • Availability to work a non-standard schedule including evening and weekend hours

What You'll Receive:

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

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday youll work in office.

  • As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.

  • Meal Subsidy available for associates who report to an office.

  • 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 our Freeport, IL office, for the Direct Sales Agent - Personal Lines I role, the pay includes a range for base pay of $38,300 annually to $$57,500 annually plus an incentive compensation structure per policy sold.

  • In our Freeport, IL office, for the Direct Sales Agent - Personal Lines II role, the pay includes a range for base pay of $41,400 - $62,000 annually plus an incentive compensation structure per policy sold.

** Compensation includes base salary, plus commissions, and the ability to earn additional monthly, quarterly, and annual incentives.

** Shift differential paid for hours worked after 5:00PM and weekends

About Sentry:

We take great pride in making Forbes list of Americas 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, were one of the largest and financially strongest mutual insurance companies in the United States. Were 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 Sr

[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 2026-01-06

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