Entry Level Insurance Jobs in Naperville, IL (NOW HIRING)

Company: Impact Insurance Agency
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person

Many teachers, coaches, and education professionals reach a point where they want to continue making a difference while also exploring new opportunities for growth, flexibility, and long-term income potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that help employees and families feel supported during life's unexpected moments. Professionals from education often thrive here because the role draws on familiar strengths: communication, mentorship, leadership, and the ability to guide others through important decisions.

This isn't about leaving education behind it's about applying your experience in a new environment where your voice, structure, and people skills continue to matter.

This entry-level outside sales role focuses on education-based conversations, relationship-building, and ongoing client support. You'll meet with business owners and employees face-to-face, helping them understand benefit options in a clear and approachable way.

As an independent contractor, you'll manage your own local territory while working within a structured system that provides training, mentorship, and consistent support even if you've never worked in sales before.

• Connect with local businesses and introduce supplemental insurance solutions
  

• Lead enrollment-style conversations that feel educational, not high-pressure
  

• Break down complex information into clear, easy-to-understand guidance
  

• Build long-term relationships through follow-up and consistent communication
  

• Organize your schedule, appointments, and territory activity
  

• Participate in weekly training, collaboration, and professional development
  

• Structured onboarding with step-by-step support
  

• Hands-on field training and mentorship
  

• Health & Life licensing assistance and reimbursement
  

• Coaching focused on communication, leadership, and relationship skills
  

• A collaborative team culture that values encouragement and growth
  

• Commission-based income with performance bonuses
  

• Average first-year income: $65,000$85,000 (performance-based)
  

• Optional 6-week base draw while building your client base
  

• Flexible daytime schedule with autonomy over your territory
  

• Long-term advancement into training, leadership, or mentoring roles
  

This opportunity may resonate with you if you:

• Have experience as a teacher, coach, trainer, educator, or mentor
  

• Enjoy presenting, guiding conversations, and helping people learn
  

• Communicate with clarity, patience, and professionalism
  

• Thrive in relationship-focused environments
  

• Are looking for a career path that blends purpose with growth potential
  

• Are willing to obtain a Health & Life Insurance license (support provided)
  

Our culture is built on mentorship, collaboration, and steady development. Many of our leaders began in entry-level roles and grew through consistency, encouragement, and a genuine desire to help others succeed. We believe strong relationships not pressure drive long-term success.

If you're ready to take your communication and leadership skills beyond the classroom and into a professional role where you can continue helping people every day, we'd love to connect.