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Outside Sales Representative - Estate Planning (Commission Only)

United Placement GroupMadison, Wisconsin🇺🇸United StatesPosted 9 Sept 2026

Why This Role Stands Out

Thrive in a role with significant earning potential through uncapped commission and bonuses, where you'll leverage provided warm leads to help families secure their futures. This hybrid position is ideal for experienced outside sales professionals who excel at in-home consultations and are motivated by commission-based success within a protected territory. Embrace this opportunity to build your career and income in estate planning.

Quick Overview

Seniority
Mid Senior
Employment type
Full Time
Work mode
Hybrid
Location
Madison, Wisconsin, United States
Posted
6 days ago
CRMCold CallingOutside Sales

Job Description

Location: Protected territory up to 100 miles of your location for producers
Compensation: $750 commission per sale, paid weekly, plus weekly and monthly production bonuses. This is a 1099 independent contractor role — there is no base salary or guaranteed income. Your skills and work ethic determine your income.

Legacy Assurance Plan provides estate planning membership plans — wills, trusts, and power of attorney documents — to families across [state]. We're hiring an outside sales representative to meet with warm, pre-qualified leads in their homes and guide them through enrollment.

What you'll do

  • Meet with warm, pre-qualified families in your assigned territory — no cold calling, no self-generated leads
  • Present and explain our estate planning membership plan, answer questions, and close enrollments
  • Manage your pipeline and follow-ups in our CRM
  • Run your own schedule within your protected territory

Compensation & structure

  • $750 commission per sale, paid weekly — no base salary
  • Weekly and monthly production bonuses on top of per-sale commission
  • Company-sponsored incentive trips for top performers
  • All leads provided at no cost to you — no lead fees, no purchased lists

What you bring

  • 3+ years of outside, in-home, or direct-to-consumer sales experience
  • A documented record of meeting or exceeding sales targets
  • Comfort using a CRM to manage a pipeline
  • Reliable personal transportation for daily in-home visits
  • Must currently reside in [state]

Good fit if: you're comfortable with 100% commission pay, prefer daily field work over office/B2B selling, and want a protected territory with company-provided leads.

Not a fit if: you need guaranteed base income or prefer inbound/office-based sales.

No license required — this is not an insurance product; we provide full product training. Apply with your current resume; qualified candidates are typically contacted within 48 hours.

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