Digital Sales Representative - Remote

Stratford Davis LLC; Chicago (IL); Remote; USD 30,000 - 70,000; Full time

Benefits offered by this job

Life policy access

Medical exchange plan options

Quarterly bonus tiers

Mentor support

Flexible calendar

Job summary

Stratford Davis LLC in Chicago, IL seeks 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 supportive team culture.

You will benefit from flexible hours, comprehensive onboarding, ongoing mentorship, and performance-based compensation with opportunities for quarterly payout tiers and career growth in a remote-friendly role.

Qualifications

• Client-first mindset and 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.

Responsibilities

• Generate prospective client leads through direct outreach and networking.
• 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-focused mindset

Verbal communication

Results-driven

Organization

Entry-level friendly

Job description

Chicago, United States | Posted on 10/29/2026

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.
• 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:

100% commission pay scale with no income ceiling.

Flexible Calendar:

Design your work hours around personal priorities.

Guided Onboarding:

Step-by-step training and ongoing mentor support.

Coverage Options:

Life policy access and medical exchange plan options.

Bonus Tiers:

Additional quarterly payout tiers and recognition programs.