True North Hotel Group jobs in Kansas City, MO - 36 jobs

Job Description Join Our Team at True North Group! Sales Agent Trainee 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 ****************************

Job Description Join Our Team at True North Group! Direct Sales Representative 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: *************************************

Job Description Join Our Team at True North Group! Direct Sales Leader Open Role: 1 Leadership Opportunity Available in Territory-Based Sales About Us At True North Group, we're committed to more than just offering supplemental insurance. We work directly with small and mid-sized companies to protect what matters most: their people. If you're passionate about helping others grow and have a talent for both selling and mentoring, we invite you to step into a leadership role with us. The Role: As a Direct Sales Leader, you'll be a representative helping businesses navigate their benefit needs, while also serving as a coach and mentor, developing new talent within your territory. You'll set the pace by example, teaching others how to prospect, present, and close with integrity. This role blends independent field work with meaningful leadership responsibilities. You'll guide new representatives through their first policies and presentations, helping them build confidence and consistency. Your success will come not just from what you achieve, but from what your team becomes under your guidance. What We're Looking For Sales Experience: You've had success in sales particularly in a field or B2B setting and understand the importance of preparation, relationship-building, and follow-through. Leadership Mindset: Whether you've led teams formally or simply mentored others along the way, you enjoy watching people grow and succeed. Clear Communicator: You can explain complex ideas simply, both one-on-one and to a group. Organized and Reliable: You follow through, track activity, and keep commitments both to clients and your team. Service-Driven: You put people first, and it shows in how you coach, how you sell, and how you lead. Licensed or License-Ready: You hold a Health & Life general lines license, or you're willing to earn it within 90 days (we'll help cover the cost and guide you through the process). What You'll Be Doing This is a field-based role with leadership responsibilities, and each week may include Personal Sales Activities: Meeting with business owners and decision-makers, giving benefit presentations to their teams, following up on leads, and setting appointments. Training & Mentoring: Shadowing new agents in the field, role-playing sales scenarios, helping others navigate their first few weeks and close their first deals. Team Development: Hosting regular check-ins, helping teammates track progress, and creating a positive, winning team culture. Goal Setting & Reporting: Working with your manager to set personal and team goals each month, and tracking key sales activities across your territory. Supporting Client Relationships: Helping both your clients and those of your team navigate claims, renewals, and benefit questions. What We Offer Hands-On Leadership Training: Tools and guidance to help you develop as both a high-performing representative and a trusted team leader. Weekly Draw Pay: A stable income base to get started, plus immediate eligibility for commission and bonuses. Performance Incentives: Quarterly retreats, annual incentive trips, stock share bonuses, and lifetime-vested renewal commissions. Career Pathways: We promote from within, team leaders can advance based on their performance to higher positions, and with larger teams. Supportive Culture: You won't do it alone. We back our leaders with strong mentorship, systems, and recognition for excellence. Flexible Hours: As you build your team and book of business, your schedule becomes more self-directed. Additional Qualifications Education: A bachelor's degree is preferred, but we'll also consider candidates with four or more years of experience in a customer-facing or sales environment. Tech Savvy: You're comfortable learning new software Salesforce and other digital tools come naturally to you. Driven and Positive: You bring energy and focus to every day and help your team do the same. Integrity and Ownership: You lead by example and take responsibility for your own success and the culture of your team. Your Next Step Starts Here At True North Group, we're growing fast and we're looking for leaders who want to build something meaningful. If you're ready to mentor others while advancing your own career, apply today. Your leadership can help shape the next generation of trusted advisors in our company. Learn more and apply at: ************************************ Let's lead the way forward,together!

True North Hotel Group , an award-winning management and development company, is seeking a Houseperson to join our team at Home2 in Kansas City, MO . We offer awesome benefits and a great family culture. RESPONSIBILITIES Responsible for assisting all housekeeping personnel in the performance of heavy duty-work as directed by the Executive Housekeeper. Maintain the cleanliness all guest corridors, floors, fireplaces, ovens, elevators and landings, linen closets, guest laundry, exercise room, employee lounge and other public areas as assigned. Assist with the removal and cleaning of soiled linens. QUALIFICATIONS High School Diploma or GED Equivalent. Must be able to move, lift, carry, push, pull and place objects weighing less than or equal to 50 pounds without assistance. Must be able to reach overhead and below the knees, including bending, twisting, pulling, and stopping. Must be able to stand, sit and/or walk for an extended period of time. Required certifications and training for TIPS, ServSafe, health department and other required organizations according to local codes. Experience in hospitality is a plus. We look forward to hearing from you! True North is an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, or genetic information.

Job Description Join Our Team at True North Group 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. ****************************

Job Description Join Our Team at True North Group! Field Sales Agent and Trainer 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. ****************************

Job Description Join Our Team at True North Group 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 software Salesforce 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. ************************************ We can't wait to see what you bring to the team!

True North Hotel Group , an award-winning management and development company, is seeking a Room Attendant to join our team at the TownePlace Suites in Leavenworth, KS . We offer awesome benefits and a great family culture. RESPONSIBILITIES Responsible for assisting all housekeeping personnel in the performance of heavy-duty work as directed by the Senior Housekeeper. Maintain the cleanliness of floors, fireplaces, ovens, elevators and landings, linen closets, guest laundry, exercise room, employee lounge and other public areas. Assist with the removal and cleaning of soiled linens. QUALIFICATIONS High School Diploma or GED Equivalent. Must be able to move, lift, carry, push, pull and place objects weighing less than or equal to 50 pounds without assistance. Must be able to reach overhead and below the knees, including bending, twisting, pulling, and stopping. Must be able to stand, sit and/or walk for an extended period of time. Required certifications and training for TIPS, ServSafe, health department and other required organizations according to local codes. Experience in hospitality is a plus. We look forward to hearing from you! True North is an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, or genetic information.

Job Description Join Our Team at True North Group! 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. ****************************

Job Description Join Our Team at True North Group! Direct Sales Leader Open Role: 1 Leadership Opportunity Available in Territory-Based Sales About Us At True North Group, we're committed to more than just offering supplemental insurance. We work directly with small and mid-sized companies to protect what matters most: their people. If you're passionate about helping others grow and have a talent for both selling and mentoring, we invite you to step into a leadership role with us. The Role: As a Direct Sales Leader, you'll be a representative helping businesses navigate their benefit needs, while also serving as a coach and mentor, developing new talent within your territory. You'll set the pace by example, teaching others how to prospect, present, and close with integrity. This role blends independent field work with meaningful leadership responsibilities. You'll guide new representatives through their first policies and presentations, helping them build confidence and consistency. Your success will come not just from what you achieve, but from what your team becomes under your guidance. What We're Looking For Sales Experience: You've had success in sales particularly in a field or B2B setting and understand the importance of preparation, relationship-building, and follow-through. Leadership Mindset: Whether you've led teams formally or simply mentored others along the way, you enjoy watching people grow and succeed. Clear Communicator: You can explain complex ideas simply, both one-on-one and to a group. Organized and Reliable: You follow through, track activity, and keep commitments both to clients and your team. Service-Driven: You put people first, and it shows in how you coach, how you sell, and how you lead. Licensed or License-Ready: You hold a Health & Life general lines license, or you're willing to earn it within 90 days (we'll help cover the cost and guide you through the process). What You'll Be Doing This is a field-based role with leadership responsibilities, and each week may include Personal Sales Activities: Meeting with business owners and decision-makers, giving benefit presentations to their teams, following up on leads, and setting appointments. Training & Mentoring: Shadowing new agents in the field, role-playing sales scenarios, helping others navigate their first few weeks and close their first deals. Team Development: Hosting regular check-ins, helping teammates track progress, and creating a positive, winning team culture. Goal Setting & Reporting: Working with your manager to set personal and team goals each month, and tracking key sales activities across your territory. Supporting Client Relationships: Helping both your clients and those of your team navigate claims, renewals, and benefit questions. What We Offer Hands-On Leadership Training: Tools and guidance to help you develop as both a high-performing representative and a trusted team leader. Weekly Draw Pay: A stable income base to get started, plus immediate eligibility for commission and bonuses. Performance Incentives: Quarterly retreats, annual incentive trips, stock share bonuses, and lifetime-vested renewal commissions. Career Pathways: We promote from within, team leaders can advance based on their performance to higher positions, and with larger teams. Supportive Culture: You won't do it alone. We back our leaders with strong mentorship, systems, and recognition for excellence. Flexible Hours: As you build your team and book of business, your schedule becomes more self-directed. Additional Qualifications Education: A bachelor's degree is preferred, but we'll also consider candidates with four or more years of experience in a customer-facing or sales environment. Tech Savvy: You're comfortable learning new software Salesforce and other digital tools come naturally to you. Driven and Positive: You bring energy and focus to every day and help your team do the same. Integrity and Ownership: You lead by example and take responsibility for your own success and the culture of your team. Your Next Step Starts Here At True North Group, we're growing fast and we're looking for leaders who want to build something meaningful. If you're ready to mentor others while advancing your own career, apply today. Your leadership can help shape the next generation of trusted advisors in our company. Learn more and apply at: ************************************ Let's lead the way forward,together!

Job Description Join Our Team at True North Group! Field Sales Agent and Trainer 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. ****************************

Job Description Join Our Team at True North Group! 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. ****************************

Job Description Join Our Team at True North Group! Direct Sales Representative 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: *************************************

Job Description Join Our Team at True North Group! Direct Sales Leader Open Role: 1 Leadership Opportunity Available in Territory-Based Sales About Us At True North Group, we're committed to more than just offering supplemental insurance. We work directly with small and mid-sized companies to protect what matters most: their people. If you're passionate about helping others grow and have a talent for both selling and mentoring, we invite you to step into a leadership role with us. The Role: As a Direct Sales Leader, you'll be a representative helping businesses navigate their benefit needs, while also serving as a coach and mentor, developing new talent within your territory. You'll set the pace by example, teaching others how to prospect, present, and close with integrity. This role blends independent field work with meaningful leadership responsibilities. You'll guide new representatives through their first policies and presentations, helping them build confidence and consistency. Your success will come not just from what you achieve, but from what your team becomes under your guidance. What We're Looking For Sales Experience: You've had success in sales particularly in a field or B2B setting and understand the importance of preparation, relationship-building, and follow-through. Leadership Mindset: Whether you've led teams formally or simply mentored others along the way, you enjoy watching people grow and succeed. Clear Communicator: You can explain complex ideas simply, both one-on-one and to a group. Organized and Reliable: You follow through, track activity, and keep commitments both to clients and your team. Service-Driven: You put people first, and it shows in how you coach, how you sell, and how you lead. Licensed or License-Ready: You hold a Health & Life general lines license, or you're willing to earn it within 90 days (we'll help cover the cost and guide you through the process). What You'll Be Doing This is a field-based role with leadership responsibilities, and each week may include Personal Sales Activities: Meeting with business owners and decision-makers, giving benefit presentations to their teams, following up on leads, and setting appointments. Training & Mentoring: Shadowing new agents in the field, role-playing sales scenarios, helping others navigate their first few weeks and close their first deals. Team Development: Hosting regular check-ins, helping teammates track progress, and creating a positive, winning team culture. Goal Setting & Reporting: Working with your manager to set personal and team goals each month, and tracking key sales activities across your territory. Supporting Client Relationships: Helping both your clients and those of your team navigate claims, renewals, and benefit questions. What We Offer Hands-On Leadership Training: Tools and guidance to help you develop as both a high-performing representative and a trusted team leader. Weekly Draw Pay: A stable income base to get started, plus immediate eligibility for commission and bonuses. Performance Incentives: Quarterly retreats, annual incentive trips, stock share bonuses, and lifetime-vested renewal commissions. Career Pathways: We promote from within, team leaders can advance based on their performance to higher positions, and with larger teams. Supportive Culture: You won't do it alone. We back our leaders with strong mentorship, systems, and recognition for excellence. Flexible Hours: As you build your team and book of business, your schedule becomes more self-directed. Additional Qualifications Education: A bachelor's degree is preferred, but we'll also consider candidates with four or more years of experience in a customer-facing or sales environment. Tech Savvy: You're comfortable learning new software Salesforce and other digital tools come naturally to you. Driven and Positive: You bring energy and focus to every day and help your team do the same. Integrity and Ownership: You lead by example and take responsibility for your own success and the culture of your team. Your Next Step Starts Here At True North Group, we're growing fast and we're looking for leaders who want to build something meaningful. If you're ready to mentor others while advancing your own career, apply today. Your leadership can help shape the next generation of trusted advisors in our company. Learn more and apply at: ************************************ Let's lead the way forward,together!

Job Description Join Our Team at True North Group Sales Representative, Entry-Level 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. ************************************

Job Description Join Our Team at True North Group! Field Sales Agent and Trainer 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. ****************************

Job Description Join Our Team at True North Group! 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. ****************************

Job Description Join Our Team at True North Group! Direct Sales Leader Open Role: 1 Leadership Opportunity Available in Territory-Based Sales About Us At True North Group, we're committed to more than just offering supplemental insurance. We work directly with small and mid-sized companies to protect what matters most: their people. If you're passionate about helping others grow and have a talent for both selling and mentoring, we invite you to step into a leadership role with us. The Role: As a Direct Sales Leader, you'll be a representative helping businesses navigate their benefit needs, while also serving as a coach and mentor, developing new talent within your territory. You'll set the pace by example, teaching others how to prospect, present, and close with integrity. This role blends independent field work with meaningful leadership responsibilities. You'll guide new representatives through their first policies and presentations, helping them build confidence and consistency. Your success will come not just from what you achieve, but from what your team becomes under your guidance. What We're Looking For Sales Experience: You've had success in sales particularly in a field or B2B setting and understand the importance of preparation, relationship-building, and follow-through. Leadership Mindset: Whether you've led teams formally or simply mentored others along the way, you enjoy watching people grow and succeed. Clear Communicator: You can explain complex ideas simply, both one-on-one and to a group. Organized and Reliable: You follow through, track activity, and keep commitments both to clients and your team. Service-Driven: You put people first, and it shows in how you coach, how you sell, and how you lead. Licensed or License-Ready: You hold a Health & Life general lines license, or you're willing to earn it within 90 days (we'll help cover the cost and guide you through the process). What You'll Be Doing This is a field-based role with leadership responsibilities, and each week may include Personal Sales Activities: Meeting with business owners and decision-makers, giving benefit presentations to their teams, following up on leads, and setting appointments. Training & Mentoring: Shadowing new agents in the field, role-playing sales scenarios, helping others navigate their first few weeks and close their first deals. Team Development: Hosting regular check-ins, helping teammates track progress, and creating a positive, winning team culture. Goal Setting & Reporting: Working with your manager to set personal and team goals each month, and tracking key sales activities across your territory. Supporting Client Relationships: Helping both your clients and those of your team navigate claims, renewals, and benefit questions. What We Offer Hands-On Leadership Training: Tools and guidance to help you develop as both a high-performing representative and a trusted team leader. Weekly Draw Pay: A stable income base to get started, plus immediate eligibility for commission and bonuses. Performance Incentives: Quarterly retreats, annual incentive trips, stock share bonuses, and lifetime-vested renewal commissions. Career Pathways: We promote from within, team leaders can advance based on their performance to higher positions, and with larger teams. Supportive Culture: You won't do it alone. We back our leaders with strong mentorship, systems, and recognition for excellence. Flexible Hours: As you build your team and book of business, your schedule becomes more self-directed. Additional Qualifications Education: A bachelor's degree is preferred, but we'll also consider candidates with four or more years of experience in a customer-facing or sales environment. Tech Savvy: You're comfortable learning new software Salesforce and other digital tools come naturally to you. Driven and Positive: You bring energy and focus to every day and help your team do the same. Integrity and Ownership: You lead by example and take responsibility for your own success and the culture of your team. Your Next Step Starts Here At True North Group, we're growing fast and we're looking for leaders who want to build something meaningful. If you're ready to mentor others while advancing your own career, apply today. Your leadership can help shape the next generation of trusted advisors in our company. Learn more and apply at: ************************************ Let's lead the way forward,together!

Job Description Join Our Team at True North Group 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 software Salesforce 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. ************************************ We can't wait to see what you bring to the team!