Entry-Level Virtual Outbound Sales Representative

Stratford Davis LLC; Chicago (IL); Remote; USD 40,000 - 70,000; Full time

Benefits offered by this job

Structured mentorship

Free digital sales tools

Fully paid trips and conferences

Job summary

Stratford Davis LLC in Chicago, IL is seeking an Entry-Level Virtual Outbound Sales Representative to learn and execute follow-up with warm leads from home. You will gain skills in conversation structure and turning interest into appointments under expert coaching.

As a beginner-friendly program, you’ll participate in structured mentorship, weekly drills, and remote consultations, with pay primarily on commission as you produce.

Qualifications

• New to sales? This virtual outbound seat teaches you to follow up with people who already raised their hand.
• Outbound follow-up with pre-qualified prospects who showed interest.
• Question frameworks that surface goals and coverage concerns quickly.
• Sell and educate outbound prospects on Life Insurance, Indexed Universal Life (IUL), and Annuities once they engage.
• Phone and video consultations from your home setup.
• Weekly skill drills with leaders who still produce themselves.

Responsibilities

• Outbound follow-up with pre-qualified prospects who showed interest.
• Question frameworks that surface goals and coverage concerns quickly.
• Sell and educate outbound prospects on Life Insurance, Indexed Universal Life (IUL), and Annuities once they engage.
• Phone and video consultations from your home setup.
• Simple recommendation building with mentor review before you present.
• Weekly skill drills with leaders who still produce themselves.

Skills

Outbound follow-up

Question frameworks

Sales education on Life Insurance/IUL/

Tools

Digital sales tools

Job description

Entry-Level Virtual Outbound Sales Representative

Chicago, United States | Posted on 11/06/2026

New to sales? This virtual outbound seat teaches you to follow up with people who already raised their hand. You will learn activity habits, conversation structure, and how to turn interest into appointments — with coaches beside you the whole way.

About the Company

We are an insurance and financial planning firm that invests in beginners. Twice honored by Entrepreneur Magazine, well rated on Glassdoor and Indeed, on the Inc. 5000 for six consecutive years, and featured by Forbes, we pair recognition with day-to-day support for new producers.

• Outbound follow-up with pre-qualified prospects who showed interest (not cold lists).
  
• Question frameworks that surface goals and coverage concerns quickly.
  
• Sell and educate outbound prospects on Life Insurance, Indexed Universal Life (IUL), and Annuities once they engage.
  
• Phone and video consultations from your home setup.
  
• Simple recommendation building with mentor review before you present.
  
• Weekly skill drills with leaders who still produce themselves.
  

Support Stack

Flexible weeks (typically 3–4 focused days). Warm outreach only. Beginner-friendly courses and live coaching. Free digital sales tools. Structured mentorship. Fully paid trips and conferences for those who rise quickly.

Pay is high commission-based from early production onward, so effort shows up in your check.