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Full time
Sales
PS

Outside Sales Representative

Platinum Supplemental InsuranceChicago, IL🇺🇸United StatesPosted Mar 27, 2026

Quick Overview

Salary
$100k/yr
Seniority
Mid Senior
Employment type
Full Time
Work mode
Hybrid
Location
Chicago, IL, United States
Outside Sales

Job Description

Outside Sales Representative | Chicago, IL, United States | Hybrid

We're hiring for a highly reputable insurance firm known for its innovative AI-powered training and commitment to employee success. This organisation offers a unique opportunity for driven individuals to build a rewarding, high-earning career with a clear path for growth and significant income potential, regardless of prior industry experience.

The Role

  • Meet face-to-face with potential clients (business owners and families) within a designated territory.
  • Educate prospects on the value and benefits of supplemental insurance products.
  • Implement a proven 10-step sales process, enhanced by AI-driven coaching.
  • Build and maintain relationships with clients to foster long-term satisfaction.
  • Collaborate with a supportive team to share best practices and achieve collective goals.

What You'll Need

  • Strong communication and interpersonal skills to connect with diverse individuals.
  • A self-starter mentality with a desire to follow a structured system and learn continuously.
  • Coachability and eagerness to leverage AI-powered training and mentorship.
  • Comfort with travel within an assigned territory Monday through Thursday.
  • A strong work ethic and motivation to drive personal income growth.

What's On Offer

  • Uncapped earning potential with typical first-year earnings of $75,000+, with lucrative residual renewal income.
  • A structured Monday-Thursday work schedule, ensuring every weekend is free.
  • Comprehensive paid training, licensing assistance, and AI-powered coaching from day one.
  • Opportunities for career advancement into leadership roles within a company that promotes from within.
  • All-expenses-paid luxury travel incentives for top performers.

Apply via Haystack today!

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