True North Group LLC.

Building client relationships, delivering benefit presentations, training new agents, and supporting team growth. | Proven outside sales or B2B sales experience, mentoring or training skills, CRM proficiency, and a health & life license or ability to obtain one. | Join 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

Engage with clients, deliver presentations, support clients, and prospect for new business. | Willingness to obtain a license, strong communication skills, and customer-facing experience. | Join Our Team at True North Group Position Title: Entry-Level Sales Representative Open Role: 1 Territory, Outside Sales Opportunity About Us: True North Group isn't just another insurance agency; We prioritize genuine relationships, outstanding service, and a positive work environment on a mission to protect small and mid-sized businesses and their employees. If you're eager to jumpstart a career where you can learn, grow, and make a difference, read on. The Role: As our newest Entry-Level Sales Representative, you'll be the face of True North in your assigned territory. You'll set your own appointments and craft a schedule that fits the rhythms of the local business community. Every day you'll: Engage with Business Owners: Visit storefronts, offices, and industrial parks to connect with decision-makers. Your goal is to understand their needs and introduce them to insurance solutions that protect their teams. Deliver Informative Presentations: Lead open-forum sessions for employee groups (anywhere from 15 to 75 people), explaining benefit packages in an easy-to-understand way. Provide Ongoing Support: From answering questions about coverage details to guiding clients through a claim, you'll become a trusted advisor who businesses rely on. Leverage Technology: Use Salesforce CRM to log client interactions, track follow-ups, and manage your pipelinekeeping everything organized and efficient. Prospect and Grow: Cold-call new prospects, follow up on leads, and ask satisfied customers for referrals. You'll be proactive, resourceful, and ready to explore every avenue to expand your book of business. Report and Collaborate: Share your weekly activity reportscalls made, meetings held, policies quotedwith your manager during team huddles. Your insights help us all improve. What we look for: Hungry to Learn: You might be new to sales, and that's perfectly fine. We'll train you from the ground up, so any drive to learn quickly will serve you well. People Person: You genuinely enjoy talking to others, asking questions, and listening carefully. Whether chatting one-on-one or speaking in front of a group, you communicate clearly and confidently. Organized & Self-Driven: Managing your own schedule in the field means you need strong organizational skills and a "get-it-done" mindset. Service-Oriented: You take pride in making others feel cared for. When a client has a concern or question, you're the one they trust to find answers. License-Ready: You either hold a Health & Life general lines license or are willing to get it within 90 days. Licensing reimbursement available. What We Offer You Hands-On Training: We combine virtual classrooms with in-field shadowing to teach you everythingfrom product knowledge to presentation best practices. Weekly Draw Pay: A guaranteed base while you build your territory, plus immediate eligibility for bonuses and commissions. Exciting Incentives: Quarterly incentive retreats, annual trips, cash bonuses, stock awards, and lifelong renewal commissions once you qualify. Climb the Ladder: Proven career paths awaitwhether you aspire to become a team leader, a field coach, or advance into agency management. Continuous Development: Regular coaching sessions, sales workshops, and leadership training help you stay sharp and elevate your game. Flexible Hours: As your client list grows, you'll have more control over your day. Work when local businesses are open and still enjoy evenings or weekends off. Additional Qualifications Education or Experience: A bachelor's degree is a plus, but if you've spent at least four years in a customer-facing environment (retail, hospitality, another sales role), we want to hear from you. Recent graduates are encouraged to apply. Tech Comfort: You're comfortable learning new softwareSalesforce and other digital tools come naturally to you. Motivation & Grit: You're coachable and thrive in a self-directed environment. Building a territory from scratch isn't easy, but the rewards are well worth it. Licensing Commitment:If you're not already licensed in Health & Life general lines, you commit to obtaining that license within three months. We take care of tuition and exam fees. How to Get Started Join True North Group, where you'll receive unwavering support, top-tier training, and the chance to build a career you can be proud of. If you're ready to roll up your sleeves, learn the ropes, and make a tangible difference in your community, this is your opportunity. https://www.thetruenorthgroupllc.com We can't wait to see what you bring to the team!

Engage with local businesses to promote insurance plans, build relationships, and support clients. | High school diploma, willingness to obtain health & life license, strong communication and organizational skills, motivation to learn. | 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 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 About the Company: True North Group LLC.

Engaging with small business owners, presenting benefit packages, guiding insurance plan selections, and building a book of business. | Willingness to get licensed in Health & Life insurance within 90 days, strong communication skills, and experience in outside sales or customer service. | Join Our Team at True North Group! Position: Field Sales Representative Number of Openings: 1 Territory Role Available Who We Are At True North Group, we believe that when people are protected, they perform betterand that starts with you. We're a team of driven professionals helping small and mid-sized businesses offer top-tier supplemental insurance to their employees. Our mission is simple: protect families, empower communities, and build careers with real purpose. This role is for someone ready to get out from behind the desk and into the fieldmeeting face-to-face with business owners, presenting to employee groups, and building long-term relationships based on trust and service. Expect to: Meet with small business owners and decision-makers Present benefit packages to groups of employees Guide individuals in selecting insurance plans that meet their needs Follow up with clients and assist with claims and coverage Build a strong personal book of business Use our CRM tools to track activity and performance Work alongside a high-performing team that trains together and wins together What We Offer This isn't just a sales jobit's a launchpad. We believe in rewarding effort, integrity, and consistent action. Here's what you can count on: Weekly Draw Pay with uncapped bonuses and commissions Day-One Training with ongoing field coaching Performance-Based Trips (think all-inclusive and unforgettable) Stock Share Bonuses & Lifetime Vested Renewal Income Growth Tracks into leadership, team building, or territory expansion Culture of Supportyou'll never be left guessing what to do next Who Thrives Here You're a fit if you: Love people and enjoy solving problems Want to build a career with freedom and purpose Are goal-oriented and self-motivated Are confident presenting in front of a group Are organized, coachable, and driven to succeed Are currently licensed orwilling to get licensed (Health & Life) within your first 90 dayswe reimburse the fees and support your preparation. Bonus Points If You Have: Previous experience in outside sales, customer service, hospitality, or athletic/competitive backgrounds Familiarity with CRM systems (Salesforce preferred but not required) A knack for leadership or mentoring others This is your chance to grow something for yourself while doing work that makes a real difference. You'll be joining a high-energy, mission-driven team that shows up with purpose every day. Apply today, and let's build something great together. www.thetruenorthgroupllc.com

Engage with business owners, deliver presentations, support clients, leverage technology, prospect and grow, report and collaborate. | Willingness to obtain a license within 90 days, strong communication and organizational skills, motivation to learn, and customer-facing experience. | Join Our Team at True North Group Position Title: Entry-Level Sales Representative Open Role: 1 Territory, Outside Sales Opportunity About Us: True North Group isn't just another insurance agency; We prioritize genuine relationships, outstanding service, and a positive work environment on a mission to protect small and mid-sized businesses and their employees. If you're eager to jumpstart a career where you can learn, grow, and make a difference, read on. The Role: As our newest Entry-Level Sales Representative, you'll be the face of True North in your assigned territory. You'll set your own appointments and craft a schedule that fits the rhythms of the local business community. Every day you'll: Engage with Business Owners: Visit storefronts, offices, and industrial parks to connect with decision-makers. Your goal is to understand their needs and introduce them to insurance solutions that protect their teams. Deliver Informative Presentations: Lead open-forum sessions for employee groups (anywhere from 15 to 75 people), explaining benefit packages in an easy-to-understand way. Provide Ongoing Support: From answering questions about coverage details to guiding clients through a claim, you'll become a trusted advisor who businesses rely on. Leverage Technology: Use Salesforce CRM to log client interactions, track follow-ups, and manage your pipelinekeeping everything organized and efficient. Prospect and Grow: Cold-call new prospects, follow up on leads, and ask satisfied customers for referrals. You'll be proactive, resourceful, and ready to explore every avenue to expand your book of business. Report and Collaborate: Share your weekly activity reportscalls made, meetings held, policies quotedwith your manager during team huddles. Your insights help us all improve. What we look for: Hungry to Learn: You might be new to sales, and that's perfectly fine. We'll train you from the ground up, so any drive to learn quickly will serve you well. People Person: You genuinely enjoy talking to others, asking questions, and listening carefully. Whether chatting one-on-one or speaking in front of a group, you communicate clearly and confidently. Organized & Self-Driven: Managing your own schedule in the field means you need strong organizational skills and a "get-it-done" mindset. Service-Oriented: You take pride in making others feel cared for. When a client has a concern or question, you're the one they trust to find answers. License-Ready: You either hold a Health & Life general lines license or are willing to get it within 90 days. Licensing reimbursement available. What We Offer You Hands-On Training: We combine virtual classrooms with in-field shadowing to teach you everythingfrom product knowledge to presentation best practices. Weekly Draw Pay: A guaranteed base while you build your territory, plus immediate eligibility for bonuses and commissions. Exciting Incentives: Quarterly incentive retreats, annual trips, cash bonuses, stock awards, and lifelong renewal commissions once you qualify. Climb the Ladder: Proven career paths awaitwhether you aspire to become a team leader, a field coach, or advance into agency management. Continuous Development: Regular coaching sessions, sales workshops, and leadership training help you stay sharp and elevate your game. Flexible Hours: As your client list grows, you'll have more control over your day. Work when local businesses are open and still enjoy evenings or weekends off. Additional Qualifications Education or Experience: A bachelor's degree is a plus, but if you've spent at least four years in a customer-facing environment (retail, hospitality, another sales role), we want to hear from you. Recent graduates are encouraged to apply. Tech Comfort: You're comfortable learning new softwareSalesforce and other digital tools come naturally to you. Motivation & Grit: You're coachable and thrive in a self-directed environment. Building a territory from scratch isn't easy, but the rewards are well worth it. Licensing Commitment:If you're not already licensed in Health & Life general lines, you commit to obtaining that license within three months. We take care of tuition and exam fees. How to Get Started Join True North Group, where you'll receive unwavering support, top-tier training, and the chance to build a career you can be proud of. If you're ready to roll up your sleeves, learn the ropes, and make a tangible difference in your community, this is your opportunity. https://www.thetruenorthgroupllc.com We can't wait to see what you bring to the team!

Drive sales, mentor new hires, lead team activities, and support community-based insurance sales. | Experience in outside sales or team leadership, current or willing to obtain health and life licenses, and strong communication skills. | Join Our Team at True North Group! Position Title: Field Sales Agent and Trainer Number of Openings: 1 Territory Leadership Position Available At True North Group, we believe leadership isn't about a title.It's about action, integrity, and raising others up. We're expanding fast, and we're looking for leaders who want to make an impact, not just earn a paycheck. As a Field Sales Agent and Trainer, you'll do more than just sell. You'll coach, mentor, and scale success. You'll be on the front lines helping new representatives hit goals, build confidence, and deliver critical protection to families and workers in your community. This is an ideal role for someone with sales experience who's ready to move into mentorship and team development. What You'll Be Doing Your mission is twofold. Drive production and build people while providing our supplemental insurance benefits to small and medium sized businesses. Your responsibilities will include: Running in-person appointments with business owners and employees Modeling high-performance sales behavior for new team members Mentoring new hires through onboarding and field training Supporting sales representatives with product knowledge and systems Leading daily or weekly team huddles to align goals Tracking production, forecasting activity, and collaborating with leadership You won't be in this aloneyou'll have top-tier mentorship and leadership support as you build your own team. What You'll Get At True North, we reward performance with leadership opportunities and growth incentives. You can expect: Weekly Draw Pay, Bonuses, and Stock Options Advanced Leadership and Coaching Development Incentive Trips, Contests and Weekly Recognition Fast-Track Growth into Agency Ownership A Collaborative Culture Focused on Impact & Integrity What You Bring to the Table We're looking for someone who leads from the front, thrives under pressure, and finds fulfillment in helping others succeed. Our ideal candidate is: A confident communicator who can coach and train others Organized, consistent, and dependable Goal-oriented, with a strong internal drive Experienced in outside sales or team leadership Passionate about making a difference and growing a team Currently licensed, or willing to get licensed (Health & Life) within your first 90 dayswe reimburse the fees and support your preparation. Bonus Points If You've Got: Experience mentoring or onboarding new hires Background in direct sales, athletics, or entrepreneurship A desire to eventually lead your own team or agency This Is Your Next Chapter This role isn't about managing from the sidelinesit's about leading from the trenches, building others up, and becoming the kind of leader you wish you had. If you are ready to build something that impacts lives - let's talk. www.thetruenorthgroupllc.com

The role involves meeting with clients, presenting benefit packages, and building a book of business. | The role requires outside sales experience, familiarity with CRM systems, and a license or willingness to obtain one within 90 days. | Join Our Team at True North Group! Position: Field Sales Representative Number of Openings: 1 Territory Role Available Who We Are At True North Group, we believe that when people are protected, they perform betterand that starts with you. We're a team of driven professionals helping small and mid-sized businesses offer top-tier supplemental insurance to their employees. Our mission is simple: protect families, empower communities, and build careers with real purpose. This role is for someone ready to get out from behind the desk and into the fieldmeeting face-to-face with business owners, presenting to employee groups, and building long-term relationships based on trust and service. Expect to: Meet with small business owners and decision-makers Present benefit packages to groups of employees Guide individuals in selecting insurance plans that meet their needs Follow up with clients and assist with claims and coverage Build a strong personal book of business Use our CRM tools to track activity and performance Work alongside a high-performing team that trains together and wins together What We Offer This isn't just a sales jobit's a launchpad. We believe in rewarding effort, integrity, and consistent action. Here's what you can count on: Weekly Draw Pay with uncapped bonuses and commissions Day-One Training with ongoing field coaching Performance-Based Trips (think all-inclusive and unforgettable) Stock Share Bonuses & Lifetime Vested Renewal Income Growth Tracks into leadership, team building, or territory expansion Culture of Supportyou'll never be left guessing what to do next Who Thrives Here You're a fit if you: Love people and enjoy solving problems Want to build a career with freedom and purpose Are goal-oriented and self-motivated Are confident presenting in front of a group Are organized, coachable, and driven to succeed Are currently licensed orwilling to get licensed (Health & Life) within your first 90 dayswe reimburse the fees and support your preparation. Bonus Points If You Have: Previous experience in outside sales, customer service, hospitality, or athletic/competitive backgrounds Familiarity with CRM systems (Salesforce preferred but not required) A knack for leadership or mentoring others This is your chance to grow something for yourself while doing work that makes a real difference. You'll be joining a high-energy, mission-driven team that shows up with purpose every day. Apply today, and let's build something great together. www.thetruenorthgroupllc.com

Assist customers at the front desk and help with inquiries. | High school diploma and basic digital skills; willingness to obtain health & life license. | 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 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

Engaging with customers and assisting at the front desk. | High school education, customer service experience, bilingual skills, and willingness to learn sales and insurance licensing. | Join Our Team at True North Group! Position: Entry-Level Sales Agent Number of Openings: 1 Territory Role Available Start Your Career with True North Group If you're ready to stop clocking in and start leveling up, welcome to True North Groupa company built around protecting families, growing leaders, and unlocking potential. We partner with small business owners to bring world-class supplemental benefits to their employees, and we're looking for energetic, coachable individuals to help us expand. We want you to provide real conversations that make a real difference. This is a ground-floor opportunity for those ready to hustle, learn, and grow into something more. What You'll Be Doing As a Sales Agent, you'll work face-to-face with business owners and employees in your area. This is an outside sales positionyou'll be out in the field, not stuck behind a desk. Your role will include: Setting and attending appointments with small businesses Presenting supplemental benefit packages to employees in group settings Helping individuals select the right coverage for their needs Following up with clients and providing ongoing support Using CRM tools to track your progress and set goals Plugging into a structured, supportive team culture What You'll Get At True North Group, we reward hustle with real benefitsnot just promises. You can expect: Weekly Draw Pay with commission and bonuses Day-One Training and ongoing mentorship Incentive Trips, Stock Bonuses, and Weekly Recognition Career Advancement Paths into Leadership and Training A Team That Invests in Your Personal Growth What We're Looking for We don't require sales experience, just the right mindset. We train the skills, you bring the energy. We're looking for someone who is: Comfortable talking with people Motivated by growth, achievement, and team wins Positive, coachable, and adaptable A fast learner who can follow systems and plans Willing to get licensed in Health & Life insurance within 30 days -we reimburse the fees and support your preparation. Extra Credit If You've Got: Bachelor's degree or associate's degree recent graduates welcome. 2 years customer service or hospitality experience A background in sports, leadership, or team-based environments Entrepreneurial drive or interest in business ownership This Isn't Just a JobIt's a Launchpad If you're looking for a "clock-in, clock-out" job, this isn't it. But if you want to grow, get paid what you're worth, and be part of something that matters then you're in the right place. Apply now, and let's get you started. www.thetruenorthgroupllc.com

Building client relationships, conducting sales presentations, and managing client accounts. | Experience in sales or customer service, ability to teach or present, and licensing in health & life insurance or willingness to obtain it. | Join Our Team at True North Group! Position: Direct Sales Representative Number of Openings: 1 Territory Sales Position Available About Us: At True North Group, we’re more than just an insurance agency – we’re dedicated to offering helpful insurance plans to small and medium-sized businesses and their employees. We believe in building real connections and providing great support. If you enjoy helping people and building lasting relationships, we want you to join us as a Direct Sales Representative. The Role: As a Direct Sales Representative at True North Group, you’ll have the freedom to set your own schedule. You’ll work during the hours that fit the businesses you’re helping. Your main job will be building strong relationships with business owners and their teams. You’ll get to know their needs and help them find the best insurance plans for their employees. You’ll meet people in person and also reach out by phone, using our easy-to-use Salesforce CRM system. Your job isn’t just about making sales – it’s about becoming a trusted advisor to your clients and helping them feel cared for. You’ll keep in touch with them, answer their questions, and support them through things like claims. What We’re Looking For: - Experience in sales or working with customers, especially outside sales. - Ability to teach others, both in person and online. - Good at staying organized and talking to people clearly. - A strong desire to help and care for others. - Health & Life general lines license, or the ability to get it within 90 days (we’ll help you with this). Position Overview: This is an outside sales job where you’ll work in your own area. You’ll be trained to visit small and medium businesses, talking to business owners and key decision-makers about our insurance products. You’ll also give presentations to groups of employees, sometimes as large as 50-100 people. Your tasks will include: - Responding to emails and phone calls from clients. - Setting up meetings to review client needs. - Attending meetings with your team or manager. - Finding new businesses, taking care of referrals, and helping current clients: Business to Business Sales. - Building and keeping up your own client list. - Working with your manager to set sales goals each month and quarter. - Building relationships with local business owners. - Setting your own work schedule and sharing it with your manager each week. - Following up on leads and cold calling new businesses in person. - Reporting your daily sales activities. We Offer: - Training both online and in the field. - Weekly draw pay with bonuses and commission eligibility upon start - Quarterly and yearly incentive trips, cash bonuses, stock share bonuses, and lifetime-vested renewal commissions. - Career growth opportunities based on how well you do. - Continued training to improve your skills and grow as a leader. - More flexible hours once you build your client list. Additional Position Qualifications: - Already licensed in Health & Life general lines, or willing to get your Health & Life license (we’ll help with the cost). - Bachelor’s degree or at least 4 years of work experience. We’ll also consider candidates finishing their degree soon or with experience in outside sales. Your New Journey: If you’re looking for a career where you can make a real difference, True North Group is the place for you. We’re excited to have a team that values honesty, care, and making a positive impact on others. Ready to grow your career in a supportive environment? Apply now and let’s make a difference together! Learn more and apply at: https://www.thetruenorthgroupllc.com/

Engage with local businesses to promote insurance plans, build relationships, and support clients. | High school diploma, willingness to obtain license, strong work ethic, and digital literacy. | 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 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

Build relationships with local businesses to sell supplemental insurance plans, conduct presentations, follow up with clients, and manage sales activities using CRM tools. | Entry-level sales skills, strong communication, willingness to obtain insurance license within 90 days, and ability to work independently in a local territory. | 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 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

Meet with business owners and employees to present and sell insurance benefit packages, build client relationships, and manage sales activities using CRM tools. | Proven sales experience, ability to present confidently, willingness to obtain Health & Life insurance licenses, and strong interpersonal and organizational skills. | Join Our Team at True North Group! Position: Field Sales Representative Number of Openings: 1 Territory Role Available Who We Are At True North Group, we believe that when people are protected, they perform betterand that starts with you. We're a team of driven professionals helping small and mid-sized businesses offer top-tier supplemental insurance to their employees. Our mission is simple: protect families, empower communities, and build careers with real purpose. This role is for someone ready to get out from behind the desk and into the fieldmeeting face-to-face with business owners, presenting to employee groups, and building long-term relationships based on trust and service. Expect to: Meet with small business owners and decision-makers Present benefit packages to groups of employees Guide individuals in selecting insurance plans that meet their needs Follow up with clients and assist with claims and coverage Build a strong personal book of business Use our CRM tools to track activity and performance Work alongside a high-performing team that trains together and wins together What We Offer This isn't just a sales jobit's a launchpad. We believe in rewarding effort, integrity, and consistent action. Here's what you can count on: Weekly Draw Pay with uncapped bonuses and commissions Day-One Training with ongoing field coaching Performance-Based Trips (think all-inclusive and unforgettable) Stock Share Bonuses & Lifetime Vested Renewal Income Growth Tracks into leadership, team building, or territory expansion Culture of Supportyou'll never be left guessing what to do next Who Thrives Here You're a fit if you: Love people and enjoy solving problems Want to build a career with freedom and purpose Are goal-oriented and self-motivated Are confident presenting in front of a group Are organized, coachable, and driven to succeed Are currently licensed orwilling to get licensed (Health & Life) within your first 90 dayswe reimburse the fees and support your preparation. Bonus Points If You Have: Previous experience in outside sales, customer service, hospitality, or athletic/competitive backgrounds Familiarity with CRM systems (Salesforce preferred but not required) A knack for leadership or mentoring others This is your chance to grow something for yourself while doing work that makes a real difference. You'll be joining a high-energy, mission-driven team that shows up with purpose every day. Apply today, and let's build something great together. www.thetruenorthgroupllc.com

Engage business owners, deliver presentations, provide ongoing support, prospect new clients, and report sales activities. | Entry-level sales experience or customer-facing experience, willingness to obtain Health & Life insurance license, strong communication and organizational skills. | Join Our Team at True North Group Position Title: Entry-Level Sales Representative Open Role: 1 Territory, Outside Sales Opportunity About Us: True North Group isn't just another insurance agency; We prioritize genuine relationships, outstanding service, and a positive work environment on a mission to protect small and mid-sized businesses and their employees. If you're eager to jumpstart a career where you can learn, grow, and make a difference, read on. The Role: As our newest Entry-Level Sales Representative, you'll be the face of True North in your assigned territory. You'll set your own appointments and craft a schedule that fits the rhythms of the local business community. Every day you'll: Engage with Business Owners: Visit storefronts, offices, and industrial parks to connect with decision-makers. Your goal is to understand their needs and introduce them to insurance solutions that protect their teams. Deliver Informative Presentations: Lead open-forum sessions for employee groups (anywhere from 15 to 75 people), explaining benefit packages in an easy-to-understand way. Provide Ongoing Support: From answering questions about coverage details to guiding clients through a claim, you'll become a trusted advisor who businesses rely on. Leverage Technology: Use Salesforce CRM to log client interactions, track follow-ups, and manage your pipelinekeeping everything organized and efficient. Prospect and Grow: Cold-call new prospects, follow up on leads, and ask satisfied customers for referrals. You'll be proactive, resourceful, and ready to explore every avenue to expand your book of business. Report and Collaborate: Share your weekly activity reportscalls made, meetings held, policies quotedwith your manager during team huddles. Your insights help us all improve. What we look for: Hungry to Learn: You might be new to sales, and that's perfectly fine. We'll train you from the ground up, so any drive to learn quickly will serve you well. People Person: You genuinely enjoy talking to others, asking questions, and listening carefully. Whether chatting one-on-one or speaking in front of a group, you communicate clearly and confidently. Organized & Self-Driven: Managing your own schedule in the field means you need strong organizational skills and a "get-it-done" mindset. Service-Oriented: You take pride in making others feel cared for. When a client has a concern or question, you're the one they trust to find answers. License-Ready: You either hold a Health & Life general lines license or are willing to get it within 90 days. Licensing reimbursement available. What We Offer You Hands-On Training: We combine virtual classrooms with in-field shadowing to teach you everythingfrom product knowledge to presentation best practices. Weekly Draw Pay: A guaranteed base while you build your territory, plus immediate eligibility for bonuses and commissions. Exciting Incentives: Quarterly incentive retreats, annual trips, cash bonuses, stock awards, and lifelong renewal commissions once you qualify. Climb the Ladder: Proven career paths awaitwhether you aspire to become a team leader, a field coach, or advance into agency management. Continuous Development: Regular coaching sessions, sales workshops, and leadership training help you stay sharp and elevate your game. Flexible Hours: As your client list grows, you'll have more control over your day. Work when local businesses are open and still enjoy evenings or weekends off. Additional Qualifications Education or Experience: A bachelor's degree is a plus, but if you've spent at least four years in a customer-facing environment (retail, hospitality, another sales role), we want to hear from you. Recent graduates are encouraged to apply. Tech Comfort: You're comfortable learning new softwareSalesforce and other digital tools come naturally to you. Motivation & Grit: You're coachable and thrive in a self-directed environment. Building a territory from scratch isn't easy, but the rewards are well worth it. Licensing Commitment:If you're not already licensed in Health & Life general lines, you commit to obtaining that license within three months. We take care of tuition and exam fees. How to Get Started Join True North Group, where you'll receive unwavering support, top-tier training, and the chance to build a career you can be proud of. If you're ready to roll up your sleeves, learn the ropes, and make a tangible difference in your community, this is your opportunity. https://www.thetruenorthgroupllc.com We can't wait to see what you bring to the team!

Engage with business owners, deliver presentations, provide ongoing support, prospect new clients, and manage sales pipeline using CRM. | Entry-level sales experience or 4+ years customer-facing experience, willingness to obtain Health & Life license within 90 days, strong communication and organizational skills. | Join Our Team at True North Group Position Title: Entry-Level Sales Representative Open Role: 1 Territory, Outside Sales Opportunity About Us: True North Group isn't just another insurance agency; We prioritize genuine relationships, outstanding service, and a positive work environment on a mission to protect small and mid-sized businesses and their employees. If you're eager to jumpstart a career where you can learn, grow, and make a difference, read on. The Role: As our newest Entry-Level Sales Representative, you'll be the face of True North in your assigned territory. You'll set your own appointments and craft a schedule that fits the rhythms of the local business community. Every day you'll: Engage with Business Owners: Visit storefronts, offices, and industrial parks to connect with decision-makers. Your goal is to understand their needs and introduce them to insurance solutions that protect their teams. Deliver Informative Presentations: Lead open-forum sessions for employee groups (anywhere from 15 to 75 people), explaining benefit packages in an easy-to-understand way. Provide Ongoing Support: From answering questions about coverage details to guiding clients through a claim, you'll become a trusted advisor who businesses rely on. Leverage Technology: Use Salesforce CRM to log client interactions, track follow-ups, and manage your pipelinekeeping everything organized and efficient. Prospect and Grow: Cold-call new prospects, follow up on leads, and ask satisfied customers for referrals. You'll be proactive, resourceful, and ready to explore every avenue to expand your book of business. Report and Collaborate: Share your weekly activity reportscalls made, meetings held, policies quotedwith your manager during team huddles. Your insights help us all improve. What we look for: Hungry to Learn: You might be new to sales, and that's perfectly fine. We'll train you from the ground up, so any drive to learn quickly will serve you well. People Person: You genuinely enjoy talking to others, asking questions, and listening carefully. Whether chatting one-on-one or speaking in front of a group, you communicate clearly and confidently. Organized & Self-Driven: Managing your own schedule in the field means you need strong organizational skills and a "get-it-done" mindset. Service-Oriented: You take pride in making others feel cared for. When a client has a concern or question, you're the one they trust to find answers. License-Ready: You either hold a Health & Life general lines license or are willing to get it within 90 days. Licensing reimbursement available. What We Offer You Hands-On Training: We combine virtual classrooms with in-field shadowing to teach you everythingfrom product knowledge to presentation best practices. Weekly Draw Pay: A guaranteed base while you build your territory, plus immediate eligibility for bonuses and commissions. Exciting Incentives: Quarterly incentive retreats, annual trips, cash bonuses, stock awards, and lifelong renewal commissions once you qualify. Climb the Ladder: Proven career paths awaitwhether you aspire to become a team leader, a field coach, or advance into agency management. Continuous Development: Regular coaching sessions, sales workshops, and leadership training help you stay sharp and elevate your game. Flexible Hours: As your client list grows, you'll have more control over your day. Work when local businesses are open and still enjoy evenings or weekends off. Additional Qualifications Education or Experience: A bachelor's degree is a plus, but if you've spent at least four years in a customer-facing environment (retail, hospitality, another sales role), we want to hear from you. Recent graduates are encouraged to apply. Tech Comfort: You're comfortable learning new softwareSalesforce and other digital tools come naturally to you. Motivation & Grit: You're coachable and thrive in a self-directed environment. Building a territory from scratch isn't easy, but the rewards are well worth it. Licensing Commitment:If you're not already licensed in Health & Life general lines, you commit to obtaining that license within three months. We take care of tuition and exam fees. How to Get Started Join True North Group, where you'll receive unwavering support, top-tier training, and the chance to build a career you can be proud of. If you're ready to roll up your sleeves, learn the ropes, and make a tangible difference in your community, this is your opportunity. https://www.thetruenorthgroupllc.com We can't wait to see what you bring to the team!

Lead outside sales efforts, train and mentor new sales agents, deliver presentations, and manage client relationships in a hybrid role. | Proven outside or B2B sales experience, sales training or coaching background, strong communication and organizational skills, ability to obtain Health & Life license, and CRM proficiency. | Join 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