Sales Representative & Field Trainer — Educators Welcome

The Impact Insurance Agency • Hales Corners, WI

2d • Hybrid

About The Position

Impact Insurance Agency is hiring a Sales Representative & Field Trainer to combine consultative business-to-business sales with mentorship and team development. The role partners with local businesses to provide supplemental insurance solutions for employees and their families. The representative meets with business leaders and employees to explain benefits, recommend insurance solutions, and support benefit-program enrollment.

The position also involves coaching newer representatives through field guidance, sharing expertise, and supporting their professional growth. It is an independent-contractor role with autonomy over territory and schedule, alongside structured guidance, ongoing training, and a collaborative, people-first culture. The posting describes the work as remote/hybrid, with local in-person client meetings, and lists Monday through Friday with weekends as needed.

The posting presents compensation in two places: the introduction lists $85,000–$105,000 per year in draw pay, commissions, and bonuses, while the Compensation & Structure section lists target earnings of $75,000–$95,000 annually. A weekly draw is available while building a book of business. Training includes step-by-step onboarding and hands-on field mentorship; licensing assistance and reimbursement are offered for Health & Life licensing. Advancement opportunities include senior sales or leadership roles.

Requirements

• Experience as a teacher, coach, mentor, or education professional with leadership experience is described as a potential fit.
• Lead with empathy, professionalism, and integrity.
• Enjoy building meaningful connections and helping others succeed.
• Thrive in collaborative, mentorship-focused environments.
• Be organized, self-motivated, and dependable.
• Be willing to obtain a Health & Life Insurance license; support is provided.

Responsibilities

• Build and nurture relationships with local business owners, leadership teams, and employees.
• Lead clear, supportive, enrollment-style presentations for client benefit programs.
• Recommend supplemental insurance solutions based on client needs.
• Mentor and coach newer representatives, providing field guidance and professional support.
• Maintain follow-ups, organized client records, and long-term account management.
• Plan and manage a schedule and sales territory.
• Participate in team collaboration, mentorship, and leadership development.

Benefits

• Health & Life licensing assistance and reimbursement.
• Weekly draw available while growing a book of business.
• Performance-based incentives and advancement into senior sales or leadership roles.
• Hybrid flexibility with local in-person client meetings.
• Step-by-step onboarding, hands-on field mentorship, and ongoing coaching and professional development.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed