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Full time
Sales

Outside Sales Representative

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

Quick Overview

Salary
$100k/yr
Work Type
Hybrid
Schedule
Full Time
Level
Mid Senior

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!

Skills

Outside Sales

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