Remote Sales Advisor (Entry Level)

Stratford Davis; Chicago (IL); Remote; USD 90,000 - 180,000; Full time

Benefits offered by this job

Training provided

Warm introductions

Real-time coaching

Health and dental cover

Bonuses

Job summary

Stratford Davis is hiring for a fully remote Life Insurance sales role. You will engage clients in meaningful conversations, assess life events, and tailor solutions such as Life Insurance, Indexed Universal Life, and Annuities.

Work from anywhere with a flexible schedule and build a book of clients. Compensation is commission-based with bonuses and six-figure earning potential when you stay proactive and serve clients well.

Qualifications

• Active listening and clear communication needed to understand client needs.
• Ability to explain complex financial products in simple terms.
• Comfort with a commission-based compensation structure.

Responsibilities

• Map the moment by learning what changed in a client’s life and what they want to protect.
• Present Life Insurance, Indexed Universal Life (IUL), and Annuities to help clients compare options.
• Recommend coverage that fits clients' timeline and budget.
• Hold video and phone appointments from wherever you work best.
• Maintain relationships after policy issuance and stay the point of contact for life changes.

Skills

Sales

Communication

Listening

Client conversations

Job description

Chicago, United States | Posted on 11/13/2026

We are an insurance and financial planning firm that starts with the moments that change a household: a first child, a new home, a career shift, or a decision to finally get organized. That client-first mindset has defined our culture as well as our growth. Entrepreneur Magazine has recognized us twice for the workplace we have built, our people continue to rate us highly on Glassdoor and Indeed, we have appeared on the Inc. 5000 list for six consecutive years, and Forbes has featured how we work with families.

What You’ll Do

Your days are built around meaningful conversations, not a script you have to repeat. Clients already asked to talk, and you help them figure out what the next chapter of their plan should look like.

• Map the moment: Learn what just changed in a client’s life and what they want to protect going forward.
  
• Walk through solutions: Sell, educate, and present Life Insurance, Indexed Universal Life (IUL), and Annuities so each option is easy to compare.
  
• Shape a practical plan: Recommend coverage that fits their timeline, budget, and the people who depend on them.
  
• Meet on their terms: Hold video and phone appointments from wherever you work best that day.
  
• Stay in the picture: Keep in touch after a policy is issued and be the person they call when life changes again.
  

What Makes Us Different

This is a fully remote role, so you can work from anywhere with a reliable connection. You set a flexible schedule around your own life instead of reporting in for a typical 8-to-5 job.

• Training provided: A clear onboarding path that covers products, conversations, and the software you will use with clients.
  
• Warm introductions: Speak with people who requested a conversation, not strangers from a cold list.
  
• Real-time coaching: Experienced leaders review your meetings and offer specific, useful feedback.
  
• Health and dental cover: Health and dental coverage is available through exchange options.
  
• Bonuses that recognize results: Performance bonuses and team incentives reward consistency.
  
• Space to advance: Step into mentoring or leadership as your book of clients grows.
  

Role Overview

This opportunity suits people who listen well, enjoy explaining complex ideas simply, and want more control over their calendar. Experience in sales is welcome but not required; teachers, nurses, service professionals, and career changers often thrive here. In this role you will sell Life Insurance, Indexed Universal Life (IUL), and Annuities to individuals and families preparing for what comes next.

Compensation is commission-based, with bonuses and six-figure earning potential for representatives who stay consistent and keep serving their clients well.