Outside Sales Representative and Trainer at True North Group LLC. Ashland, KY

Downtown Boulder Partnership; Ashland (KY); Hybrid; USD 40,000 - 70,000; Full time

Benefits offered by this job

Leadership Training

Weekly Draw Pay

Performance-Based Incentives

Career Advancement

Flexible Hours

Job summary

True North Group in Ashland is looking for an Outside Sales Representative and Trainer. This role combines outside sales with field leadership and offers opportunities for career advancement.

The ideal candidate should have experience in outside sales, mentoring or coaching abilities, and a strong desire to help others succeed. We provide leadership training, reliable income, performance-based incentives, and a collaborative culture. Apply today to make a lasting impact!

Qualifications

• 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 to various audience sizes.

Responsibilities

• Meet with business owners to understand their needs and offer insurance plans.
• Deliver engaging benefit presentations to employee groups.
• Shadow new reps and provide hands-on sales training.

Skills

Outside sales experience

Mentoring and coaching

Strong communication skills

Organizational skills

Health & Life general lines license

Education

Bachelor’s degree or equivalent experience

Tools

Salesforce

Job description

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 through 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.