Outside Sales Representative And Trainer

Allegiant Business Group; Friendswood (TX); On-site; USD 60,000 - 120,000; Full time

Benefits offered by this job

Draw program

Licensing assistance

Training materials

Flexible scheduling

Job summary

Allegiant Business Group is seeking an Outside Sales Representative And Trainer to join our local territory team. This boots-on-the-ground role focuses on meeting business owners, delivering benefit presentations, and coaching new reps through ride-alongs and mentorship.

As a 1099 contractor, you will build your book of business while helping others grow, with travel within your territory and non-remote, face-to-face engagements.

Qualifications

• Proven outside or B2B sales success in benefits, insurance, or related fields.
• Experience mentoring or coaching sales professionals in the field.
• Strong presentation skills for 1:1 and group settings.
• Organized, systematic approach to coaching and development.
• Familiarity with CRM systems and data-driven coaching.

Responsibilities

• Serve as a dependable outside sales producer in your territory.
• Deliver clear, professional benefit presentations to business owners and employee groups.
• Conduct ride-alongs, debriefs, role-plays, and field coaching for reps.
• Develop training materials, playbooks, and short coaching modules.
• Partner with leadership to set activity goals and improve conversion metrics.
• Maintain your clientportfolio while supporting team growth and retention.

Skills

Outside sales

B2B sales

Mentoring / training

Presentation skills

CRM Salesforce

Licensed health & life insurance

Tools

Salesforce

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.