Outside Sales Representative

Overview

Join Our Team at True North Group

Position: Outside Sales Representative

Number of Openings: 1 Territory Role Available

True North Group is an insurance partner for small and mid-sized businesses, delivering personalized supplemental insurance solutions and exceptional service. We protect what matters most: their people. If you thrive on building relationships and helping others, this Outside Sales Representative role may be for you.

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

• Relationship-Builder:
  You are energized by meeting new people and earning their trust.
• Self-Starter:
  You manage your own calendar, follow through on leads, and set ambitious goals.
• Clear Communicator:
  You explain complex information simply—one-on-one or to groups of up to 75.
• Organized & Tech-Savvy:
  You keep detailed records in Salesforce and manage follow-ups meticulously.
• Service-Oriented:
  You care about clients’ well-being and guide them through claims and policy questions with empathy.
• Licensed or Ready:
  You hold (or will obtain within 90 days) a Health & Life general lines license; fees are reimbursed and preparation supported.

In this outside sales position, you will:

• Prospect & Connect:
  Identify local businesses, engage with the community, and schedule discovery meetings.
• Present Solutions:
  Lead tailored benefits presentations for business owners and employee groups.
• Maintain Relationships:
  Respond 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:
  Participate in 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.

If you’re ready to hit the ground running, forge meaningful client relationships, and grow a rewarding career in outside sales, True North Group is here to support you every step of the way.

Apply now and let’s protect our community, together.

Learn more and apply at: