Digital Sales Representative - Remote

Stratford Davis LLC; Chicago (IL); Remote; USD 30,000 - 120,000; Full time

Job summary

Stratford Davis LLC is seeking a motivated individual to help expand our client footprint across the United States through remote outreach and personalized proposals.

You will learn how to identify prospects, present tailored proposals on Life Insurance, Indexed Universal Life (IUL), and Annuities, and manage client accounts within a supportive, team-focused culture. This fully remote role offers flexible hours and uncapped commissions.

Qualifications

• Entry-level applicants welcome; full training curriculum provided.
• Client-first mindset and high personal accountability.
• Strong verbal communication and confidence on video calls.
• Results-driven with a commission-based compensation model.
• Organized with a productive remote work schedule.

Responsibilities

• Generate prospective client leads through direct outreach and networking.
• Sell, educate, and present to clients on Life Insurance, Indexed Universal Life (IUL), and Annuities.
• Draft and deliver customized proposals tailored to client needs.
• Provide consistent follow-up to convert leads into long-term accounts.
• Attend weekly team meetings to share best practices and build skills.

Skills

Client-first mindset

Verbal communication

Video call confidence

Results-driven

Remote scheduling

Entry-level friendly

Job description

Chicago, United States | Posted on 11/07/2026

About the Opportunity

We are seeking a motivated individual to help expand our client footprint. You will learn how to identify prospects, present custom proposals, and manage client accounts within a highly supportive, team-focused culture.

Core Responsibilities

• Generate prospective client leads through direct outreach and networking.
• Sell, educate, and present to clients on Life Insurance, Indexed Universal Life (IUL), and Annuities.
• Draft and deliver customized proposals tailored to client needs.
• Provide consistent follow-up to convert leads into long-term accounts.
• Attend weekly team meetings to share best practices and build skills.

Qualifications

• Client-first mindset combined with high personal accountability.
• Strong verbal communication skills and confidence on video calls.
• Results-driven attitude suited for a performance commission model.
• Organized approach to maintaining a productive remote schedule.
• Entry-level applicants welcome, full training curriculum provided.

Performance Compensation

commission-only pay structure with no income ceiling.

Flexible Calendar

Design your work hours around personal priorities.

Guided Onboarding

Step-by-step training and ongoing mentor support.

Training is provided, with ongoing mentorship. This fully remote role lets you work from anywhere with flexible hours rather than a typical 8-to-5 schedule. Compensation is high and commission-only, with uncapped commissions based on the business you place.