Sales Representative Entry-Level

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

Start Your Career with Purpose

If you're ready to start a career that's flexible, meaningful, and full of opportunity, we'd love to meet you. At True North Group, we'll help you build something you can be proud of—one client and one conversation at a time.

Apply now and begin your journey with us today.

https://www.thetruenorthgroupllc.com