Executive Assistant - Insurance Agency Operations

Since launching from scratch in 2002, Paula Simmons COUNTRY Financial has grown to serve over 1,600 households with a reputation for excellence, integrity, and precision. We take pride in doing things right the first time and providing personalized insurance solutions with care and expertise. Our small, close-knit team operates like family. Each person plays a critical role, and every contribution is valued.

Led by a Hall of Fame agent with a 24-year streak of top honors, our office is a place where high standards meet genuine heart.

We are seeking an experienced Executive Assistant with a strong insurance agency operations background to serve as our agent's right hand and the operational backbone of our office. This is a senior role for a proven professional who can handle a high volume of client interactions every day, keep every detail accurate, and make every client feel they are in capable hands.

What we offer

• Base salary of $60,000 to $80,000 per year, based on experience
• Performance bonuses
• Retirement plan
• Health Insurance
• Monday through Friday schedule
• Direct partnership with a nationally recognized, Hall of Fame agent

• Paid Time Off (PTO)
• Health Insurance
• Mon-Fri Schedule
• Retirement Plan

• Partner directly with the agent: manage the calendar, correspondence, client meeting preparation, and follow-through
• Own a high volume of daily client interactions by phone, email, and in person, giving every client clear answers and clear next steps
• Process and quality-check policy changes and new business across auto, home, life, commercial, and financial lines
• Conduct policy reviews that strengthen coverage and client retention
• Oversee billing inquiries, payments, and past-due follow-up
• Coordinate with underwriting, claims, and carrier home office to resolve issues quickly
• Build and refine office workflows, checklists, and documentation so work gets done right the first time
• Support compliance, recordkeeping, and the day-to-day readiness of the office
• Serve as a knowledgeable resource for other team members

These requirements are non-negotiable. Please only apply if you have all of the below requirements met.

• 2+ years of insurance agency experience (captive or independent), including time in a senior service, account management, or operations role
• Illinois Property & Casualty license required
• Life license preferred or obtained within 180 days
• A proven track record of accuracy and professionalism under heavy volume
• Excellent written and verbal communication, including the ability to explain coverage and billing in plain language
• Proficiency with agency management systems and Microsoft 365, and quick to master new software
• Discretion with confidential client and financial information