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Entry-Level Outside Sales Representative -- Teachers, Coaches & Educators Welcome

The Impact Insurance Agency
Portage, WI Other
POSTED ON 4/14/2026
AVAILABLE BEFORE 5/9/2026
Entry-Level Outside Sales Representative Teachers, Coaches & Educators Welcome

Company: Impact Insurance Agency
Pay: $65,000$85,000 average first-year income | Commission Optional 6-Week Base Draw
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person


A Career Path for People Who Naturally Support Others

Many educators and coaches reach a moment where they want to keep helping people grow just in a new environment that offers flexibility, professional development, and long-term earning potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that support employees and their families during life's unexpected moments. Teachers, mentors, and trainers often find this role to be a natural extension of what they already do best: building trust, encouraging others, and guiding meaningful conversations.

If you're someone who leads with empathy, enjoys connecting with people, and finds purpose in helping others succeed, this opportunity offers a rewarding next chapter.


The Opportunity

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

You don't need previous sales experience. Our structured training program is designed specifically for individuals transitioning from education, coaching, or other service-driven roles.

As an independent contractor, you'll manage your own local territory while working within a collaborative environment that provides mentorship, guidance, and consistency.


What You'll Do
  • Build genuine relationships with local business owners and their teams

  • Lead enrollment-style conversations that feel educational rather than sales-driven

  • Listen carefully and offer thoughtful, people-focused solutions

  • Support onboarding, follow-ups, and long-term client relationships

  • Manage appointments, scheduling, and territory activity

  • Participate in weekly collaboration, coaching, and professional development


Training & Support
  • Step-by-step onboarding designed for educators transitioning careers

  • Hands-on field mentorship and real-world learning

  • Health & Life licensing assistance and reimbursement

  • Coaching focused on communication, leadership, and relationship-based service

  • A collaborative culture built on encouragement, not pressure


Compensation & Structure
  • 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

  • Advancement opportunities into mentoring, training, or leadership roles


Ideal Background

This opportunity may resonate with you if you:

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

  • Enjoy helping people feel confident in their decisions

  • Communicate with warmth, patience, and professionalism

  • Thrive in relationship-driven environments

  • Value collaboration and meaningful impact in your work

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


Why Impact Insurance Agency

Our culture is built around service, collaboration, and genuine encouragement. Many of our leaders started in entry-level roles and grew through mentorship, consistency, and a strong desire to help others succeed both clients and teammates alike.


Apply Today

If you're ready to take the communication and leadership skills you've built in education and apply them in a people-focused professional career, we'd love to connect.

https://www.theimpactinsuranceagency.com/

Salary : $65,000 - $85,000

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