Outside Sales Representative and Trainer

True North Group LLC.; Westfield (IN); On-site; USD 60,000 - 100,000; Full time

Benefits offered by this job

Leadership Training

Weekly Draw Pay

Performance-Based Incentives

Career Advancement

Collaborative Culture

Flexible Hours

Job summary

True North Group is seeking an Outside Sales Representative and Trainer to lead in our local territory. You will sell to business owners, present to employee groups, and train new agents to build their careers. This role blends mentorship with high‑performing field sales and offers room for leadership growth.

Ideal candidates have proven outside/B2B sales experience, strong presentation skills, and a willingness to obtain a Health & Life license within 90 days.

Qualifications

• Proven outside/B2B sales experience.
• Experience mentoring or training sales teams.
• Strong presentation and communication skills in small groups and large audiences.
• CRM experience, preferably Salesforce; adept at maintaining client records.

Responsibilities

• Meet with business owners to assess needs and propose tailored insurance plans.
• Deliver engaging benefit presentations to employee groups.
• Support clients through claims and coverage questions.
• Shadow and train new reps; lead call reviews and prep sessions.
• Help reps set weekly activity goals and track progress.
• Collaborate with manager to build a high-performing sales team.
• Grow your own book of business while mentoring others.

Skills

Outside sales

Coaching

Presentation skills

Salesforce CRM

Time management

Education

Bachelor’s degree or equivalent

Tools

Salesforce

Job description

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 insurance—we 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 an Outside 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 week—selling 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 theirs—coaching, 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 confidently—whether 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

• 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 team—you’ll help shape the future of our company.