Outside Sales Pro & Field Coach - 1099 Contractor

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

Benefits offered by this job

Licensing assistance

Draw program

Job summary

Allegiant Business Group seeks an Outside Sales Representative and Trainer for a local territory in a boots-on-the-ground role. You will primarily sell in the market, present benefits to owners and employee groups, and coach newer reps through ride-alongs and mentoring.

This 1099 contractor position combines field sales with leadership duties, including developing training materials and playbooks, while supporting team growth and client retention.

Qualifications

• 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.

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.

Skills

Outside sales

B2B sales

Mentoring

CRM & Salesforce

Tools

Salesforce

Job description

Allegiant Business Group seeks an Outside Sales Representative and Trainer for a local territory in a boots-on-the-ground role. You will primarily sell in the market, present benefits to owners and employee groups, and coach newer reps through ride-alongs and mentoring.

This 1099 contractor position combines field sales with leadership duties, including developing training materials and playbooks, while supporting team growth and client retention.