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Legacy Planning

Sales Professional – Entrepreneurial Opportunity

Legacy Planning

Independent life insurance sales contractor helping Chicago families protect their finances. Building client pipelines and books of business through warm inbound leads and a proven sales system.

Posted 8/9/2026contractRemote • Illinois • 🇺🇸 United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates strong sales acumen and the ability to build and manage a client pipeline while following a proven system. Capable of working independently and self-motivated to achieve personal and team growth.

Highest-signal resume keywords
Sales ExperienceClient Relationship ManagementPipeline DevelopmentIndependent Contractor ExperienceInsurance License Acquisition

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Soft Skills
Self-MotivatedCoachableIndependent Work
Tools & Technologies
Proprietary Lead System
Certifications & Qualifications
Insurance License
Industry Keywords
Life InsuranceProtection SolutionsClient-Facing RoleDaily Activity CommitmentReferral Management

About the role

Key responsibilities & impact
  • Connect with interested clients through the proprietary lead system
  • Present life insurance and protection solutions tailored to each family's situation
  • Follow the step-by-step system for consistent daily activity and follow-up
  • Build and manage a pipeline of active clients and referrals
  • Build an independent book of business
  • Grow at an individual pace and potentially build a team

Requirements

What you’ll need
  • Self-motivated and able to work independently
  • Experience in sales, real estate, finance, customer service, or another client-facing role
  • Insurance experience is not required
  • Coachable and willing to follow a proven system
  • Located in or serving the Chicago area
  • Willing to obtain an insurance license if not already licensed
  • Able to commit to consistent daily activity and follow-up
  • Must accept an independent contractor, commission-only arrangement with no guaranteed income

Benefits

Comp & perks
  • Carrier-paid bonuses
  • Mentorship from agents who are actively producing
  • Warm inbound leads system; no cold calling
  • Ownership model and overrides as you grow a team
  • Flexible schedule
  • Opportunity to work part-time or full-time
  • Build a book of business with ongoing policy payments