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Licensed Insurance Agent - Chicago North

Kemper · Milwaukee, WI · Full time

Posted Sep 15, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about your sales results as a licensed agent. What did you sell, and how did you track your numbers?

What they are checking: Whether they have a real, measurable track record and understand their own sales activity.

This role involves frequent home visits to collect premiums and sell policies. How do you feel about that kind of field schedule?

What they are checking: Whether they truly want in-home field work, since it's very different from phone or office-based insurance sales.

The role pays uncapped commissions. How do you keep chasing commission from pushing you into sales that aren't right for the customer?

What they are checking: Whether they have the integrity to turn down a bad sale even when it would pay them more.

Tell me about a time you turned an unhappy customer into a loyal one.

What they are checking: Whether they can recover trust after a problem, which keeps a book of business from shrinking.

What would you do

You'd be assigned an established book of business. What would you do in your first month with those existing customers?

What they are checking: Whether they would protect and build on the existing book first, rather than chasing only new sales.

A long-time customer has missed two premium payments. How do you handle the visit?

What they are checking: Whether they can protect the policy and the relationship with empathy, without pushing someone into hardship.

How do you find new customers along a route when you're already busy serving existing ones?

What they are checking: Whether they know how to generate referrals and leads from the people they already serve.

About the work

How do you explain the difference between term and whole life insurance to a family on a tight budget?

What they are checking: Whether they know their products and can match them honestly to a modest-income family's real needs.

What's an example of a suitability or compliance rule you follow when selling life insurance?

What they are checking: Whether they understand regulatory duties like suitability and replacement rules, which protect customers and their license.

How do you keep accurate records of collections and policy changes when you're in the field all day?

What they are checking: Whether they are organized with money and paperwork, since mistakes in collections are a serious problem.

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The full job description

As published by Kemper.

Location(s) Milwaukee, Wisconsin Details Kemper is one of the nation’s leading specialized insurers. Our success is a direct reflection of the talented and diverse people who make a positive difference in the lives of our customers every day. We believe that a high-performing culture, combined with valuable opportunities for personal development and professional challenge, and a healthy work-life balance, can be highly motivating and productive. Kemper’s products and services are making a real difference to our customers, who have unique and evolving needs. By joining our team, you will help provide an experience to our stakeholders that delivers on our promises. Role: Licensed Insurance Sales Agent (with sign-on bonus and uncapped commissions). Employment Type : Full-Time with Benefits Work Arrangement : Field Role Career and Opportunity : Kemper is a diversified insurance holding company that has been in business for over 100 years. We are firmly committed to serving the insurance needs of modest-income families. Our strength lies in our dedication to frequent personal home visits with new and existing customers to collect premiums, conduct sales of new policies, and address other service needs. Kemper Life is actively seeking licensed agents to join our field sales teams. As a licensed insurance agent, you will be assigned an established book of business that provides prospecting opportunities for new sales and immediate income through a collections commission for premiums collected each month. With Kemper’s pay-for-performance compensation model, agents have the opportunity to determine their own income. As your book of business expands, so does your earning potential. Exceptional performance is also recognized through awards, prizes, and company-sponsored trips. If you’re passionate about serving the underserved, this is the career for you. Our agents gain personal satisfaction and community prestige by performing meaningful work that helps clients protect the people and property they cherish. The compensation for the role is fully commission-based. Benefits: Kemper offers competitive benefits, including: • Major Medical and Dental Insurance • Group Life Insurance • Short-Term & Long-Term Disability • 401(k) with Company Match • Paid Vacation • Great work-life balance. Benefit from autonomy in managing your customer visits and premium collection schedule • Career growth and promotional opportunities Licensed Agent Bonus Program Through Kemper’s Licensed Agent Bonus Program, new agents who are licensed to sell all Kemper Life Products will be eligible for up to $4,750 in bonuses during their first year. • $750 bonus when hired and assigned to an agency • $1,500 bonus after six production months • $2,500 bonus after 12 production months *To qualify for these bonuses, agents must maintain a $200 average monthly issued premium and be an active employee in good standing. Agents must be fully licensed to sell all Kemper Life products in his/her resident state. The Licensed Agent Bonus Program is not available to rehires or agents with temporary licenses. Responsibilities: Day-to-Day Activities : • Coordinating home visits and conducting sales presentations, recommending products, and closing new sales • Prospecting for new sales opportunities • Maintaining strong customer relationships by collecting premiums on a pre-arranged schedule that you determine • Responding promptly to service requests such as beneficiary changes, claims, and loans • Record keeping, accounting for money collected, and processing policy paperwork Agent Expectations: • Grow the assigned territory through new sales • Build strong working relationships with customers • Devote the time necessary to fulfill the responsibilities of the role • Pursue continuous professional development in insurance products and sales effectiveness Minimum Qualifications: • Must be fully licensed to sell all Kemper Life’s products (Life, Health, P&C) • Customer service experience • Must be at least 18 years of age • Valid driver’s license with required auto insurance coverage • Dependable vehicle for daily travel • Ability to pass a background check, motor vehicle report, and drug screening • Authorization to work in the United States Opportunity is knocking. Don’t let it pass you by! Kemper is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, disability status, or any other status protected by the laws or regulations in the locations where we operate. We are committed to supporting diversity and equality throughout our organization, and we work diligently to maintain a workplace that is free from discrimination. Kemper does not accept unsolicited resumes through or from search firms or staffing agencies. All unsolicited resumes will be considered the property of Kemper, and Kemper will not be obligated to pay a placement fee. Kemper will never request personal information, such as your social security number or banking information, via text or email. Additionally, Kemper does not use external messaging applications, such as WireApp or Skype, to communicate with candidates. 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