Entry Level Sales Representative (Remote)

Stratford Davis LLC; Chicago (IL); Remote; USD 42,000 - 58,000; Full time

Benefits offered by this job

Flexible schedule

Comprehensive training

Mentorship

Job summary

Stratford Davis LLC is seeking an Entry Level Sales Representative to work remotely while based in Chicago, IL. You will engage pre-qualified leads, assess client needs, and deliver virtual consultations to tailor insurance solutions. The role includes comprehensive training and ongoing mentorship to help you thrive.

This entry-level position emphasizes entrepreneurship with support, offering flexible scheduling and the potential for uncapped commissions as you grow within the company.

Qualifications

• Entry-level role with comprehensive training.
• Pre-qualified leads provided; no cold calling.
• Remote-friendly with mentorship and growth opportunities.

Responsibilities

• Working closely with mentors in a collaborative setting.
• Connecting with pre-qualified leads to evaluate their financial and insurance needs.
• Conducting virtual consultations via Zoom or phone.
• Designing customized insurance solutions based on client goals.
• Presenting recommendations to guide clients toward decisions.

Skills

Lead qualification

Virtual consultations

Needs assessment

Presentation skills

Mentorship access

Tools

Zoom

Job description

Entry Level Sales Representative (Remote)

Chicago, United States | Posted on 10/27/2026

Join a High-Performing Team in Financial Services

Who We Are

We are a fast-growing insurance and financial services company known for our results-driven culture and dedication to excellence. Our workplace has been recognized multiple times for its outstanding environment, earning accolades from Entrepreneur Magazine, consistently strong reviews on Glassdoor and Indeed, and a place on the Inc. 5000 list for six straight years. We’ve also recently been featured in Forbes.

What You’ll Do

As a member of our team, you’ll be supported with continuous training and mentorship designed to help you thrive. Your responsibilities will include:

• Working closely with experienced mentors in a collaborative setting
  


• Connecting with pre-qualified leads to evaluate their financial and insurance needs
  


• Conducting virtual consultations via Zoom or phone
  


• Designing customized insurance solutions based on client goals
  


• Presenting recommendations clearly to guide clients toward confident decisions
  

Why Join Us

• We focus on efficiency and results, not just long hours. Here’s what makes this opportunity stand out:
  


• Flexible schedule, typically 3–4 focused days per week
  


• No cold calling - leads are warm and pre-qualified
  


• Free, comprehensive training with ongoing support
  


• Earn six income within the 1st year following our streamline steps
  


• Performance-based compensation with uncapped commission potential
  


• Access to advanced sales tools at no cost
  


• Direct mentorship from experienced professionals
  


• Incentive-based international travel opportunities for top performers
  

About the Role

This position centers on financial products such as Indexed Universal Life (IUL) insurance, annuities, and life insurance. It’s a great fit for self-motivated individuals seeking the independence of entrepreneurship with the support of a proven system.

If you’re looking to take ownership of your career, build financial independence, and make a real difference in people’s lives, we encourage you to apply and begin your path to success.