Outside Sales Representative

Join Our Team at True North Group

Position:
Outside Sales Representative

Number of Openings: 1 Territory Role Available

At True North Group, we’re more than an insurance agency—we’re trusted partners to small and mid-sized businesses. Our mission is to protect what matters most: their people. We do this by delivering personalized supplemental insurance solutions and exceptional service. If you’re someone who thrives on building relationships and helping others, this Outside Sales Representative role was made for you.

As an Outside Sales Representative, you’ll be on the front lines of our business, visiting local companies in your assigned territory. You’ll discover each client’s unique needs, guide them through our range of insurance products, and become a trusted advisor they can rely on. With the freedom to set your own schedule, you’ll balance in-person visits with strategic phone outreach, all supported by our intuitive Salesforce CRM.

• Relationship-Builder:
  Energized by meeting new people and earning their trust.
• Self-Starter:
  Manages your own calendar, follows through on leads, and sets ambitious goals.
• Clear Communicator:
  Explains complex information simply—whether one-on-one or presenting to groups of up to 75.
• Organized & Tech-Savvy:
  Keeps detailed records in Salesforce and never lets a follow-up slip through the cracks.
• Service-Oriented:
  Cares about clients’ well-being, guiding them through claims and policy questions with empathy.
• Licensed or Ready:
  Holds (or will obtain within 90 days) a Health & Life general lines license—fees reimbursed and preparation supported.

• Prospect & Connect:
  Identify local businesses, connect with the community, and schedule discovery meetings.
• Present Solutions:
  Lead tailored benefits presentations for business owners and employee groups.
• Maintain Relationships:
  Respond promptly to calls and emails, manage renewals, and assist clients through claims.
• Track Your Pipeline:
  Use Salesforce to log interactions, manage tasks, and measure progress.
• Collaborate with Your Team:
  Join weekly strategy sessions to share best practices and celebrate wins.
• Set Your Own
  
  Hours:
  
  Build a schedule that fits the businesses you serve—early mornings, late afternoons, or midday visits.

• Comprehensive Training:
  Blend of virtual workshops and ride-along field sessions to get you client-ready.
• Weekly Draw Pay:
  Steady income floor plus immediate eligibility for bonuses and commissions.
• Incentive Rewards:
  Quarterly retreats, annual trips, cash bonuses, stock awards, and lifetime-vested renewal commissions.
• Career Growth:
  Clear pathways to senior sales roles, field training positions, or agency leadership.
• Supportive Culture: A team that shares resources, mentors new reps, and celebrates collective success.
• Flexible
  
  Schedule:
  
  More autonomy over your hours as you build your client base.

• Bachelor’s degree or a minimum of 4 years in a customer-facing role—recent graduates welcome.
• Comfort with technology—Salesforce experience is a plus.
• Coachable attitude and a drive to exceed goals.