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Outside Sales Representative

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

Why This Role Stands Out

This hybrid Outside Sales Representative role offers uncapped earning potential with a typical first-year income of $75,000-$100,000, plus residual income and bonuses, while providing a fantastic work-life balance with every weekend off. You'll thrive here if you're a motivated individual eager to leverage a proven system and comprehensive training to build a rewarding, high-earning career in sales, and you're encouraged to apply to learn more.

Quick Overview

Salary
$75k - $100k/yr
Seniority
Mid Senior
Employment type
Full Time
Work mode
Hybrid
Location
Bolingbrook, IL, United States
Outside Sales

Job Description

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

This employer is a well-established insurance provider known for its innovative AI-powered training and supportive growth environment. They are seeking driven individuals to build rewarding, high-earning careers, offering a proven system and dedicated back-office support to ensure success from day one. This is an excellent opportunity for self-starters looking for uncapped income potential and a strong work-life balance.

The Role

  • Meet with business owners and families within your territory Monday through Thursday to educate them on supplemental insurance needs.
  • Utilize a proven 10-step sales process, enhanced by AI coaching, to build rapport and close deals.
  • Travel within your assigned territory for in-person client meetings.
  • Collaborate with a supportive team to share best practices and drive collective success.
  • Identify and engage with prospective clients needing supplemental insurance protection.

What You'll Need

  • Strong communication and interpersonal skills for connecting with diverse clients.
  • A self-starting attitude with a willingness to learn and follow a structured sales system.
  • Comfort with overnight travel Monday through Thursday within an assigned territory.
  • A results-driven mindset focused on controlling and maximizing personal income.
  • Demonstrable work ethic and commitment to consistent self-improvement.

What's On Offer

  • Uncapped earning potential with significant first-year income ($75,000+ typical, $100,000+ achievable).
  • Residual renewal income and performance bonuses for ongoing financial growth.
  • A consistent three-day weekend every week with no evening or Saturday work.
  • Comprehensive paid training, licensing assistance, and ongoing AI-powered coaching.
  • Opportunities for career advancement and luxury travel incentives.

Apply via Haystack today!

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