Work-From-Anywhere Sales Representative

Stratford Davis LLC; Chicago (IL); Remote; USD 60,000 - 120,000; Full time

Job summary

Stratford Davis LLC, a Chicago-based insurance and financial planning firm, is seeking a remote role that lets you work from anywhere with a flexible schedule. Training is provided and you’ll meet households nationwide via video and phone, discovering goals and protecting families with life insurance, IUL, and annuities.

You’ll give clear recommendations and provide thoughtful follow-up to ensure clients feel supported post-decision, all while earning commissions with uncapped potential.

Qualifications

• Experience in consultative sales and presenting options clearly.
• Ability to educate clients about life insurance products.
• Comfort working remotely with flexible schedule.

Responsibilities

• Meet households by video and phone from any location.
• Listen to clients to identify protections and goals.
• Educate clients on Life Insurance, IUL, and Annuities.
• Provide clear recommendations.
• Follow up to ensure client support after decision.

Skills

Video consultations

Phone consultations

Needs assessment

Client education

Communication

Job description

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

We are an insurance and financial planning firm built for people who want meaningful client work without being tied to an office. Our workplace has been honored twice by Entrepreneur Magazine, and our teams earn consistently high ratings on Glassdoor and Indeed. Six consecutive years on the Inc. 5000 list, plus a recent Forbes feature, reflect how we grow and how we lead.

What You'll Do

• This is a fully remote seat. You can work from anywhere, set a flexible schedule, and skip the typical 8-to-5 grind. Full training and mentorship are provided. Your focus will include:
• Nationwide Conversations: Meet households by video and phone from whatever location works for you.
• Goal Discovery: Listen closely to what each family wants to protect and what they hope to build.
• Client Education: Educate clients on Life Insurance, Indexed Universal Life (IUL), and Annuities.
• Clear Recommendations: Turn those conversations into straightforward options they can understand.
• Thoughtful Follow-Up: Stay present after the decision so clients feel supported, not rushed.

Why People Choose Us

• We designed this role around freedom and support, not rigid office hours:
• Work From Anywhere: This is a remote role - no commuting and no required workplace.
• A Schedule You Shape: Structure your week around high-value conversations instead of a fixed 8-to-5 clock.
• Warm Introductions: Speak with interested, pre-screened prospects rather than chasing cold lists.
• Training Provided: Full training and mentorship are provided so you can grow with guidance from experienced leaders.
• Tools Ready to Use: Digital platforms and proprietary resources are supplied so you can focus on clients.
• Room to Grow: A supportive team and a path to larger responsibility as your results expand.

Role Overview

• What You Offer: The solutions in this role are Life Insurance, Indexed Universal Life (IUL), and Annuities.
• Who Fits: Motivated professionals who want location independence and a career that rewards initiative.
• How You Earn: Compensation is high and commission-only. Your income tracks the results you produce, with uncapped earning potential.