Outside Sales Representative And Trainer

Job Description

Job Description

Join Allegiant Business Group - Outside Sales Representative And Trainer

Location: Local Territory, Face-to-Face

About Allegiant Business Group

Allegiant Business Group provides practical supplemental benefit solutions to small and mid-sized employers. We value steady service, clear communication, and developing field professionals who put clients first. As we expand, we're looking for a hands-on sales professional who can both sell in the market and train others to do the same — operating with the flexibility of a contractor arrangement.

The Role

This is a field-first position that blends outside sales with practical training duties. You'll spend most of your time in the market: meeting business owners, delivering benefit presentations to employee groups, and coaching newer reps through ride-alongs and one-on-one mentoring. You'll continue to grow your own book of business while helping others become reliable, consistent performers.

This is not a remote trainer role - it's boots-on-the-ground work paired with leadership responsibilities, delivered as a 1099 contractor engagement.

Key Responsibilities

Serve as a dependable outside sales producer in your assigned territory.

Deliver clear, professional benefit presentations to business owners and employee groups.

Conduct ride-alongs, call/meeting debriefs, role-plays, and field coaching for new and developing reps.

Develop and maintain concise training materials, playbooks, and short coaching modules.

Work with leadership to set realistic activity goals and improve conversion metrics.

Maintain your own client portfolio while supporting the growth and retention of your team's production.

Compensation & Support

Commission-based compensation that delivers worth based on your effort.
Incentives to entice the best out of our agents, adding additional earnings upon their commission.

A draw program to allow for extra financial security.

Licensing assistance and training materials; scheduling flexibility for training sessions.

What We're Looking For

Demonstrated success in outside sales or B2B sales, ideally within benefits, insurance, or related fields.

Prior experience mentoring, training, or coaching sales professionals in the field.

Strong presentation skills — comfortable with 1:1 meetings and groups of 20–75+.

Organized, practical, and steady — you follow systems and help others do the same.

Familiarity with CRM systems (Salesforce preferred) and a data-driven approach to coaching.

Licensed in Health & Life insurance, or willing to obtain licensure within 90 days (Allegiant supports this process).

Reliable transportation and willingness to travel regularly within your territory.

Why This Role Matters

You'll directly influence how our clients are served and how new reps develop. By combining consistent production with thoughtful coaching, you expand our reach while helping others build durable careers in the field.

How to Apply

If you have field experience, a practical coaching style, and are comfortable operating as an independent contractor, we'd like to hear from you. Please apply through our careers page or send your resume and a brief note about your training/sales experience to our recruiting team.