Outside Sales Representative and Trainer at The True… · Westfield

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

This is a hybrid role combining outside sales and field leadership. Weekly responsibilities include:

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.

Apply now and start building something meaningful.

https://www.thetruenorthgroupllc.com