Sales Representative Entry-Level

True North Group LLC.; Lake Oswego (OR); On-site; USD 35,000 - 60,000; Full time

Benefits offered by this job

Thorough Training

Weekly Draw Pay

Exciting Incentives

Career Advancement

Continued Development

Flexible Hours

Job summary

True North Group LLC in Lake Oswego, Oregon, is seeking an Entry-Level Sales Representative to grow a local client base by offering our supplemental insurance solutions to small and mid-sized businesses. This outside-sales role lets you work in your territory, with training, a proven system, and a supportive team.

You’ll build relationships, present to groups, and guide business owners and employees—earning through base pay, draws, bonuses, and commissions as you develop your book of business.

Qualifications

• A people-person who enjoys conversation and building relationships.
• Motivated, self-driven, and ready to learn.
• Great communicator—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 Health & Life license within 90 days; we'll help cover costs and provide study support.

Responsibilities

• Visit local businesses to present our supplemental insurance offerings.
• Meet with business owners and present to groups of employees (often 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

Self-motivated

Good communicator

Organizational skills

Helping mindset

Licensing within 90 days

Education

High school diploma

Bachelor's degree preferred

Customer service experience preferred

Tools

Salesforce

CRM 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

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.