Remote Insurance Strategy Sales Representative

Stratford Davis; Boston (MA); Remote; USD 90,000 - 140,000; Full time

Job summary

Stratford Davis offers a remote Insurance Strategy Sales Representative position in Boston, MA. The role focuses on consultative conversations about life insurance, indexed universal life, and annuities, with a scalable referral-driven pipeline and coaching support.

You will manage discovery calls, coverage mapping, and tailored recommendations, while navigating a high commission-based pay structure. Calendar control and travel with top producers are highlighted benefits.

Qualifications

• Experience in life insurance sales or financial planning is a plus.
• Ability to map coverage against client needs and gaps.
• Strong consultative selling and communication skills required.

Responsibilities

• Conduct discovery calls to understand household income, dependents, and priorities.
• Map current coverage against risk gaps and present tailored options.
• Explain Life Insurance, IUL, and Annuities and how they meet client timelines.
• Design straightforward recommendations aligned to client risk tolerance.
• Guide clients through next steps and stay available after paperwork is complete.

Skills

Life Insurance

Indexed Universal Life (IUL)

Annuities

Job description

Remote Insurance Strategy Sales Representative

Boston, United States | Posted on 11/10/2026

Our firm helps families and professionals put durable insurance and financial planning in place. We have been recognized twice by Entrepreneur Magazine for the quality of our workplace, maintain strong ratings on Glassdoor and Indeed, have appeared on the Inc. 5000 list for six consecutive years, and were recently highlighted in Forbes for how we grow and lead in this industry.

What You’ll Do

• You will spend your days in focused client conversations, supported by coaching and a ready pipeline. Typical work includes:
  
• Discovery Calls: Meet virtually with interested households to understand income, dependents, and long-term priorities.
  
• Coverage Mapping: Compare current protection, if any, against the gaps that would leave a family exposed.
  
• Product Conversations: Educate clients on Life Insurance, Indexed Universal Life (IUL), and Annuities.
  
• Recommendation Design: Build straightforward options that match each client's timeline and comfort with risk.
  
• Follow-Through: Walk approved clients through next steps and stay available after the paperwork is complete.
  

What Makes Us Different

• We designed this seat so your time goes into advising, not chasing strangers:
  
• A Calendar You Control: Most producers concentrate their client work into about three or four productive days each week.
  
• Introductions, Not Cold Lists: Prospects come pre-interested, so you are not grinding through unsolicited dials.
  
• Learning Without Tuition: Digital course libraries and live coaching stay open to you at no charge.
  
• Modern Sales Stack: You receive the same digital platforms and proprietary tools our top producers use.
  
• Side-by-Side Mentors: Experienced leaders review your calls and help you tighten your process.
  
• Producer Travel: Leading results can unlock fully paid annual conferences and international trips.
  

Role Overview

• What You Offer: The role is built around Life Insurance, Indexed Universal Life (IUL), and Annuities—the vehicles we use to help clients protect income and prepare for future needs.
  
• Who Thrives Here: Independent, coachable professionals who want ownership of their book without building a company from scratch.
  
• How You Are Paid: This is a high commission-based role. Your income rises and falls with the business you place, without an artificial ceiling.