Field Sales Leader & Mentor (1099 Contractor)

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

Job summary

Allegiant Business Group is seeking an Outside Sales Representative and Trainer to operate in a local territory with face-to-face client meetings. This field-based role blends sales production with hands-on coaching, ride-alongs, and structured training for advancing reps.

As a 1099 contractor, you will build your book of business while mentoring others, delivering compelling benefit presentations, and helping teams reach higher conversion through practical playbooks and data-driven coaching.

Qualifications

• Proven success in outside or B2B sales, preferably in benefits or insurance.
• Experience mentoring or coaching sales reps in the field.
• Strong presentation skills for 1:1 meetings and groups 20–75+.
• Excellent organizational skills and adherence to systems.
• Familiarity with CRM systems (Salesforce preferred) and data-driven coaching.
• Licensed in Health & Life insurance or willing to obtain licensure within 90 days.
• Reliable transportation and willingness to travel within territory.

Responsibilities

• Serve as outside sales producer in 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

Presentation skills

CRM (Salesforce)

Data-driven coaching

Travel willingness

Education

Health & Life Insurance licensing

Job description

Allegiant Business Group is seeking an Outside Sales Representative and Trainer to operate in a local territory with face-to-face client meetings. This field-based role blends sales production with hands-on coaching, ride-alongs, and structured training for advancing reps.

As a 1099 contractor, you will build your book of business while mentoring others, delivering compelling benefit presentations, and helping teams reach higher conversion through practical playbooks and data-driven coaching.