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Insurance Sales Pros: Market Is | Outside Sales

Remote / Online - Candidates ideally in
Milwaukee, Milwaukee County, Wisconsin, 53244, USA
Listing for: United Placement Group
Remote/Work from Home, Commission-based only position
Listed on 2026-10-04
Job specializations:
  • Sales
    Insurance Sales
Salary/Wage Range or Industry Benchmark: 60000 - 90000 USD Yearly USD 60000.00 90000.00 YEAR
Job Description & How to Apply Below
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.

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