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Insurance Agent - Book Opportunity - Flossmoor, IL

COUNTRY Financial Agency · Flossmoor, IL · Full time

Posted Sep 10, 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

Why Flossmoor? What ties do you have to the area, and what do you know about the people who live there?

What they are checking: Whether they have real ties to or knowledge of the community, since local trust is what builds this business.

What insurance experience makes you ready to manage a book from day one?

What they are checking: Whether their licensing, product knowledge and service track record fit a role that needs an experienced agent now.

Tell me about a time you inherited accounts or work from someone else. What did you keep and what did you change?

What they are checking: Whether they can step into someone else's system with care and improve it without disrupting customers.

What would you do

You would be taking over an established, active book. What do you do in your first 30 days?

What they are checking: Whether they have a plan to meet clients and keep them before anyone considers leaving.

A client who was loyal to the previous agent says they may move their policies. How do you respond?

What they are checking: Whether they can earn trust from a skeptical client without getting defensive or overpromising.

Flossmoor is a south suburb of Chicago, and much of this book is likely to be established homeowners and retirees. How would you make sure you can serve them well from day one?

What they are checking: Whether they can match their skills to the clients already in the book and close gaps quickly.

How would you decide what to change about the office and staff you inherit?

What they are checking: Whether they value continuity for clients while still taking full ownership of how the office runs.

A client is angry about a renewal increase and wants you to fix it. What do you do?

What they are checking: Whether they explain rate changes honestly and look at real options instead of just losing the client.

How would you work with COUNTRY Trust Bank Financial Advisors to build the financial services side of this book?

What they are checking: Whether they can spot clients who need retirement or investment help and refer them naturally.

About the work

What numbers would you look at first to understand the health of a book you are taking over?

What they are checking: Whether they think in retention, policies per household and loss trends, not just total premium.

How would you find growth inside the book without making existing clients feel sold to?

What they are checking: Whether they review accounts for single-line households and real coverage gaps instead of pushing products.

Practice this interview out loud.

Offer builds a real interview for this exact role at COUNTRY Financial Agency from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by COUNTRY Financial Agency.

We’re looking for an experienced insurance professional to manage an established and active book of business. This book is positioned for continued growth across the full line of COUNTRY Financial® products and services. COUNTRY Financial® Insurance Agents have the opportunity and the autonomy to build a rewarding, financially stable career while enriching lives in the communities we serve. The Career Our insurance agents take a consultative approach to grow business with existing and prospective clients. As independent contractors, they are in business for themselves but not by themselves, and they: • Diversify their income through our portfolio of property and casualty, life and health lines. • Have the flexibility to manage their schedules to balance their careers and personal interests. • Educate clients and prospects about our products and services. • Collaborate with COUNTRY Trust Bank® Financial Advisors to inform clients of our financial products and services. • Establish an office and build a staff. We Offer COUNTRY Financial® Insurance Agents have uncapped earning potential and: • Opportunities to earn performance-based global trips and financial rewards. • Access to continued learning and marketing resources. • Affiliation with our 100-year-old brand heritage and family-focused culture that values authenticity and integrity. • There is no buy-in required. Qualifications Successful COUNTRY Financial® Insurance Agents are: • Entrepreneurial, motivated, and goal driven. • A strong communicator with excellent business acumen. • Committed to linking your efforts with tangible rewards. • Passionate about making positive impacts in their communities. Required Licenses* • Property/Casualty State Insurance License* • Life/Health State Insurance License* Preferred Experience • Bachelor’s Degree • 2+ years of experience in the insurance and or financial services industry • 5+ years of business ownership or managerial experience About Us COUNTRY Financial® is the trade name for a collective of affiliated insurance and financial services companies. This means we have an extended family of support and a large backing. Since 1925, COUNTRY Financial has been dedicated to helping others plan for their future while also protecting what matters most to them. What started long ago as a simple commitment on Midwest farmlands has expanded to become a FORTUNE 1000 insurance and financial services organization proudly serving 19 states. Our insurance agents, financial advisors, and employees remain dedicated to serving nearly one million households with our diverse range of personal and business insurance products as and financial services products. And our consistent AM Best A+ rating means we have the financial strength to keep the promises we make to our clients. *These licenses are not required to apply; however, the candidate’s ability to obtain these licenses is essential when a contract decision is made. **The Premiums and AUC indicated above are the estimated amounts. These amounts may change and are not guaranteed. Future value/size will depend on the strategies, tactics, and efforts of the agent, in addition to external factors including but not limited to pricing trends in the marketplace, competitive intensity, consumer preferences, client relationships, etc. ***Farm Certifications are done annually in January. If marked “Yes”, the agent must obtain certification the following January as a condition of the agent’s contract. COUNTRY Financial® is the marketing name for the COUNTRY Financial family of affiliated companies (collectively, COUNTRY), which include COUNTRY Life Insurance Company®, COUNTRY Mutual Insurance Company®, and their respective subsidiaries, located in Bloomington, Illinois. Investment management, retirement, trust, and planning services provided by COUNTRY Trust Bank®. The investment objectives, risks, charges, and expenses of an investment company should be carefully considered before investing.

Apply at COUNTRY Financial Agency