Sales Representative Entry-Level

Company: True North Group LLC.
Location: Winter Garden
Posted on: February 13, 2026

Job Description:

Job Description Job Description Join Our Team at True North Group Position: Sales Representative, Entry-Level Number of Openings: 1 Territory Sales Position Available About Us At True North Group, we believe great careers are built on real relationships. We're a people-first supplemental insurance agency focused on helping small and mid-sized businesses protect what matters most: their families and employees. Whether you're just starting your professional journey or looking for a fresh start, this entry-level sales opportunity is the perfect launchpad. We'll give you the training, tools, and support to 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

Keywords: True North Group LLC., Orlando , Sales Representative Entry-Level, Sales , Winter Garden, Florida