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Insurance Sales Pros: A Better Market Is Waiting | Outside Sales

United Placement Group
Janesville, Wisconsin, United States; Kenosha, Wisconsin, United States; Madison, Wisconsin, United States; Marshfield, Wisconsin, United States; Milwaukee, Wisconsin, United States Posted Oct 2, 2026
Full-time

About this role

Insurance Sales Pros: A Better Market Is Waiting | Outside Sales – Estate Planning | Legacy Assurance Plan

If you've built your career selling insurance, you already know how to sit at a kitchen table and earn a family's trust. Now imagine putting those skills to work in a market that isn't saturated, in a territory that's yours alone, with less chargeback risk hanging over every sale.

Why estate planning beats insurance

  • A wide-open market. Most American families still don't have an estate plan, so you're not fighting over the same prospects every other agent is calling.
  • No competing against your own. Your protected territory (up to 100 miles) is yours. No other Legacy Assurance Plan rep works your leads.
  • Less chargeback risk. You're not living with the lapse-and-clawback cycle that comes with insurance policies.
  • Warm leads only. Every appointment is with a family who already asked to learn about estate planning.
  • No license needed. It's not an insurance product, so there's nothing to maintain or renew.

What you'll do

  • Meet with warm, pre-qualified families in their homes

  • Explain wills, trusts, and powers of attorney, and help families enroll in our estate planning membership plan

  • Our network attorneys handle the legal work, and your home office handles the rest

  • Pay

  • $750 commission per sale, paid weekly

  • Weekly and monthly production bonuses, plus incentive trips for top performers

  • 1099, commission-only. No base salary or guaranteed income.

  • What you need

  • 3+ years of outside, in-home, or direct-to-consumer sales experience (insurance sales experience is a strong plus)

  • Comfortable with 100% commission

  • Reliable transportation and comfort with a CRM

  • Currently live in [State]

  • Your sales skills transfer. The headaches don't. Apply with your current resume.

Your next opportunity starts here

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