Join Our Team at True North Group!
Position: Sales Agent Trainee
Number of Openings: 1 Territory Sales Position Available
Break Into Sales with Purpose
Looking to launch your career in a role where your results directly impact your paycheck. At True North Group, we believe the best salespeople aren't born -they're trained. If you're hungry to learn, ready to hustle, and eager to grow into something more, we'll give you the tools to make it happen.
If you're looking for more than a job something that offers real growth, real income potential, and the chance to make a difference this could be it.
Your Day-to-Day Will Include:
Meeting with individuals and teams in person
Presenting workplace supplemental insurance benefits and protecting families
Following up and generating leads and building your own pipeline
Collaborating with teammates and mentors in and out ofthe field
Learning to close deals and manage long-term client relationships
We Provide:
Uncapped weekly commission + Weekly draw pay + bonus structure
Comprehensive training and field development
Incentive trips, team events, and networking opportunities
A clear, personalized career path from day one
It is a requirement that you obtain your Health and Life Insurance license before beginning work with us. Once you receive a job offer, our onboarding team will guide you through the licensing process step-by-step. After you join our team, you'll be eligible for reimbursement of any licensing fees you paid to become licensed.
What You Need:
A positive attitude and strong work ethic
Excellent communication skills
A coachable mindset and eagerness to learn
The ability to work independently and manage time
Reliable transportation and professional presence
No Experience, No Problem.
Whether you're just out of university, switching industries, or trying to find a place to grow long term, we've built a system that helps newcomers thrive. Many of our top reps came in with zero sales experience ? just the willingness to work hard, take feedback, and stay consistent.
We're interviewing now. Take the first step toward something bigger.
Apply at www.thetruenorthgroupllc.com
Read LessJoin 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 succeedno 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' availabilitywhile being backed by a proven system and a supportive team.
Your job isn't just about making salesit'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 communicatorboth 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 1050+ 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 ofone client and one conversation at a time.
Apply now and begin your journey with us today.
https://www.thetruenorthgroupllc.com
Join Our Team at True North Group
Position: Territory Sales Representative
Number of Openings: 1 Territory RepresentativePosition Available
Build a Career That Builds People
At True North Group, we believe in protecting familiesand empowering individuals to take ownership of their future. That starts with our people.
As aTerritory Sales Representative, you'll meet face-to-face with working-class families and employees across your assigned territory. You'll provide them with affordable supplemental insurance benefits that offer peace of mind when life throws them something unexpected.
This is more than direct salesthis is service with purpose, backed by a team that wins together and grows together.
In this role, you'll:
Conduct in-person meetings with business owners and employees
Deliver tailored supplemental benefit presentations in group or individual settings
Build trust and long-term relationships with clients
Generate and follow up on leads, maintain records, and close new accounts
Partner with experienced leaders and trainers to refine your approach
Tap into mentorship, field training, and proven systems
What's In It for You
We believe hard work should come with big rewards. Here's what you'll gain:
Uncapped Commission + Weekly Draw Pay + Performance Bonuses and Incentives
Fast-Paced Career Progression & Promotion Tracks
Ongoing Education, Licensing Support, and Mentorship
Exclusive Incentive Trips + Stock Bonuses + Recognition
A Clear Mission with Measurable Impact
You Might Be a Fit If You're:
Motivated, resilient, and ready to learn
Professional and people-oriented
Competitive, coachable, and growth-driven
Comfortable working independently in a field-based role
Willing to obtain a Life & Health license within 30 days (support in obtaining, and reimbursement afterwards)
Bonus Points For:
Background in customer service, retail, or athletics
Previous experience with team environments
Entrepreneurial spirit or business-minded goals
True North Group Is Hiring Now
This is a rare chance to launch a career that pays for performance, promotes from within, and gives back through purpose-driven work.
Apply today and start building the version of yourself you've been aiming for.
www.thetruenorthgroupllc.com
Read LessJoin Our Team at True North Group
Position: Outside Sales Representative
Number of Openings: 1 Territory Role Available
About True North Group
At True North Group, we're more than an insurance agencywe're trusted partners to small and mid-sized businesses. Our mission is to protect what matters most: their people. We do this by delivering personalized supplemental insurance solutions and exceptional service. If you're someone who thrives on building relationships and helping others, this Outside Sales Representative role was made for you.
The Role
As an Outside Sales Representative, you'll be on the front lines of our business, visiting local companies in your assigned territory. You'll discover each client's unique needs, guide them through our range of insurance products, and become a trusted advisor they can rely on. With the freedom to set your own schedule, you'll balance in-person visits with strategic phone outreach, all supported by our intuitive Salesforce CRM.
What We're Looking For
Relationship-Builder: You're energized by meeting new people and earning their trust.
Self-Starter: You manage your own calendar, follow through on leads, and set ambitious goals.
Clear Communicator: You explain complex information simplywhether one-on-one or presenting to groups of up to 75.
Organized & Tech-Savvy: You keep detailed records in Salesforce and never let a follow-up slip through the cracks.
Service-Oriented: You genuinely care about clients' well-being, guiding them through claims and policy questions with empathy.
Licensed or Ready: You hold (or will obtain within 90 days) a Health & Life general lines licensewe reimburse the fees and support your preparation.
Position Overview
In this outside sales position, you will:
Prospect & Connect: Identify local businesses, connect with the community, and schedule discovery meetings.
Present Solutions: Lead tailored benefits presentations for business owners and employee groups.
Maintain Relationships: Respond promptly to calls and emails, manage renewals, and assist clients through claims.
Track Your Pipeline: Use Salesforce to log interactions, manage tasks, and measure your progress.
Collaborate with Your Team: Join weekly strategy sessions to share best practices and celebrate wins.
Set Your Own Hours: Build a schedule that fits the businesses you serveearly mornings, late afternoons, or midday visits.
We Offer
Comprehensive Training: Blend of virtual workshops and ride-along field sessions to get you client-ready.
Weekly Draw Pay: Steady income floor plus immediate eligibility for bonuses and commissions.
Incentive Rewards: Quarterly retreats, annual trips, cash bonuses, stock awards, and lifetime-vested renewal commissions.
Career Growth: Clear pathways to senior sales roles, field training positions, or agency leadership.
Supportive Culture: A team that shares resources, mentors new reps, and celebrates collective success.
Flexible Schedule: More autonomy over your hours as you build your client base.
Additional Qualifications
Bachelor's degree or a minimum of 4 years in a customer-facing rolerecent graduateswelcome.
Comfort with technologySalesforce experience is a plus.
Coachable attitude and a drive to exceed goals.
Your New Journey Starts Here
If you're ready to hit the ground running, forge meaningful client relationships, and grow a rewarding career in outside sales, True North Group is here to support you every step of the way.
Apply now and let's protect our community, together.
Learn more and apply at: https://www.thetruenorthgroupllc.com/
Read LessJoin Our Team at True North Group!
Position: Outside Sales Representative and Trainer
Number of Openings: 1 Territory Leadership Position Available
About Us
At True North Group, we do more than offer supplemental insurancewe empower people. We partner with small and mid-sized businesses to provide benefit solutions that protect what matters most: their employees and families. But just as importantly, we invest in our own team. If you have a passion for helping others succeed, leading by example, and building strong client relationships, we want you on our side as anOutside Sales Representative and Trainer.
The Role
As an Outside Sales Representative and Trainer, you'll be a cornerstone of our team in your local territory. You'll be out in the field each weekselling to business owners, presenting to groups of employees, and training new agents as they begin their careers. Your role is part mentor, part high-performing sales representative, and fully invested in both personal and team success.
You'll lead from the front by building your own client base, then guide others as they build theirscoaching, role-playing, and troubleshooting along the way. This is a dynamic, boots-on-the-ground leadership role with plenty of room to grow.
What We're Looking For
Proven experience in outside sales or business-to-business sales
Experience mentoring, coaching, or training others in a sales setting
Ability to present clearly and confidentlywhether 1-on-1 or to a room of 50+
Strong organizational skills, follow-through, and CRM usage
A desire to serve, support, and grow those around you
A Health & Life general lines license, or the ability to obtain one within 90 days (we'll help with this process)
Position Overview
This is a hybrid role combining outside sales and field leadership. Weekly responsibilities include:
Meeting with business owners to understand their needs and offer tailored insurance plans
Delivering engaging benefit presentations to employee groups
Following up with clients and supporting them through claims and coverage questions
Shadowing new reps in the field and providing hands-on sales training
Running call reviews, prep sessions, and debriefs with new team members
Helping new reps track progress and set weekly activity goals
Collaborating with your manager to build a strong, successful sales team
Maintaining and growing your own book of business while guiding others to do the same
We Offer
Leadership Training: Hands-on support to grow your leadership skills and train effectively in the field
Weekly Draw Pay: Reliable income with bonuses and commissions starting on day one
Performance-Based Incentives: Quarterly and annual trips, cash bonuses, stock share awards, and lifetime-vested renewal commissions
Career Advancement: Clear paths into senior leadership, regional expansion, or training roles as you develop
Collaborative Culture: A team that celebrates wins, shares knowledge, and grows together
Flexible Hours: Build your schedule around client needs and your team's availability
Additional Qualifications
Bachelor's degree or equivalent experience in sales, leadership, or coaching
Experience using CRM software (we use Salesforce)
A coachable, positive attitude and a desire to help others win
Strong time management and communication skills
Lead from the Front
If you're ready to grow your career while guiding others toward success, this is your chance to make a lasting impact. At True North Group, you won't just lead a teamyou'll help shape the future of our company.
Apply now and start building something meaningful.
https://www.thetruenorthgroupllc.com
Read LessJoin Our Team at True North Group!
Position: Sales Agent Trainee
Number of Openings: 1 Territory Sales Position Available
Break Into Sales with Purpose
Looking to launch your career in a role where your results directly impact your paycheck. At True North Group, we believe the best salespeople aren't born -they're trained. If you're hungry to learn, ready to hustle, and eager to grow into something more, we'll give you the tools to make it happen.
If you're looking for more than a job something that offers real growth, real income potential, and the chance to make a difference this could be it.
Your Day-to-Day Will Include:
Meeting with individuals and teams in person
Presenting workplace supplemental insurance benefits and protecting families
Following up and generating leads and building your own pipeline
Collaborating with teammates and mentors in and out ofthe field
Learning to close deals and manage long-term client relationships
We Provide:
Uncapped weekly commission + Weekly draw pay + bonus structure
Comprehensive training and field development
Incentive trips, team events, and networking opportunities
A clear, personalized career path from day one
It is a requirement that you obtain your Health and Life Insurance license before beginning work with us. Once you receive a job offer, our onboarding team will guide you through the licensing process step-by-step. After you join our team, you'll be eligible for reimbursement of any licensing fees you paid to become licensed.
What You Need:
A positive attitude and strong work ethic
Excellent communication skills
A coachable mindset and eagerness to learn
The ability to work independently and manage time
Reliable transportation and professional presence
No Experience, No Problem.
Whether you're just out of university, switching industries, or trying to find a place to grow long term, we've built a system that helps newcomers thrive. Many of our top reps came in with zero sales experience ? just the willingness to work hard, take feedback, and stay consistent.
We're interviewing now. Take the first step toward something bigger.
Apply at www.thetruenorthgroupllc.com
Read Less