← Back to Jobs
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
Similar jobs
Part Sales Manager - Part Time
AutoZone · Whitehall, United States
14 minutes agoPart Sales Manager - Part Time
AutoZone · Collinsville, United States
14 minutes agoPart Sales Manager - Part Time
AutoZone · Knoxville, United States
14 minutes agoSales Specialist
Atlas Copco Group · Houston, United States
15 minutes agoLife Sales Agent
Automobile Club Of Missouri · Saint Louis, United States
16 minutes agoLife Sales Agent
Automobile Club Of Missouri · Kansas City, United States
16 minutes ago$29/hr