Sales Representative Entry-Level

True North Group LLC.; Winchester (KY); On-site; USD 40,000 - 64,000; Full time

Benefits offered by this job

Thorough Training

Weekly Draw Pay

Incentives & bonuses

Career advancement

Development support

Flexible hours

Job summary

True North Group LLC. is seeking an Entry-Level Sales Representative to build relationships with local businesses in your territory. You will learn to assess employee benefit needs and present supplemental insurance plans, while working with a flexible schedule and a proven system of support.

You will gain training, work with a supportive team, and have the opportunity to earn commissions and bonuses from day one. Prior insurance experience is not required, and licensing is supported.

Qualifications

• People-person who enjoys conversation and building relationships.
• Motivated, self-driven, and ready to learn.
• Great communicator in 1:1 and group settings.
• Strong organizational habits and follow-up.
• Willingness to obtain Health & Life license within 90 days.

Responsibilities

• Visit businesses and introduce our supplemental insurance offerings.
• Meet with business owners and present to groups of employees (10-50+).
• Respond to client questions via phone and email.
• Set appointments, conduct follow-ups, and support clients through claims.
• Use Salesforce CRM to track activities, contacts, and progress.
• Work closely with your manager to set and meet sales goals.
• Build your own client base and develop long-term relationships.
• Share your weekly schedule and results with your manager.

Skills

People skills

Motivation & learning

Communication

Organizational skills

Help mindset

Licensing readiness

Education

High school diploma

Bachelor's degree

Tools

Salesforce

Email & Calendar tools

Job description

Join Our Team at True North Group

Position: Sales Representative, Entry-Level

Number of Openings: 1 Territory Sales Position Available

About Us

At True North Group, we believe great careers are built on real relationships. We're a people-first supplemental insurance agency focused on helping small and mid-sized businesses protect what matters most: their families and employees. Whether you're just starting your professional journey or looking for a fresh start, this entry-level sales opportunity is the perfect launchpad. We'll give you the training, tools, and support to succeed - no prior insurance experience needed.

The Role

As an Entry-Level Sales Representative, you'll get to know local businesses in your territory, learn about their employee benefit needs, and offer supplemental insurance plans that make a difference. You'll have the freedom to create your own schedule and work in a way that fits your clients' availability - while being backed by a proven system and a supportive team.

Your job isn't just about making sales - it's about making connections. You'll build trust, provide guidance, and become a valuable resource to the business owners and employees you serve.

What We're Looking For

• A people-person who enjoys conversation and building relationships
• Someone who's motivated, self-driven, and ready to learn
• Great communicator - both one-on-one and in front of a group
• Strong organizational habits and attention to follow-up
• A genuine desire to help others and make a positive impact
• Willingness to obtain a Health & Life general lines license within 90 days (we'll help cover the cost later and provide study support)

Position Overview

This is an outside sales role, where you'll work locally in your own territory. You'll be trained to:

• Visit businesses and introduce our supplemental insurance offerings
• Meet with business owners and present to groups of employees (often 10-50+ at a time)
• Respond to client questions via phone and email
• Set appointments, conduct follow-ups, and support clients through claims
• Use our Salesforce CRM to track your activities, contacts, and progress
• Work closely with your manager to set and meet sales goals
• Build your own client base and develop long-term relationships
• Share your weekly schedule and results with your manager

We Offer

• Thorough Training: Get up to speed with both online and in-the-field coaching
• Weekly Draw Pay: Steady income as you build your book of business, with bonuses and commissions available from day one
• Exciting Incentives: Quarterly trips, cash bonuses, stock share awards, and lifetime-vested renewal commissions
• Career Advancement: Clear pathways to grow into leadership, training, or higher-level sales roles based on your performance
• Continued Development: Ongoing support to help you grow your skills and your confidence
• Flexible Hours: You'll have the freedom to design your workday around your business clients' availability

Additional Qualifications

• High school diploma required; a bachelor's degree or customer service experience is a plus
• Strong work ethic and willingness to learn new skills
• Comfortable using basic digital tools (email, calendar, CRM systems)
• Already licensed in Health & Life, or ready to get licensed within 90 days