Sales Representative Entry-Level
True North Group LLC.
Job Description
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
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.
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