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Full time
Sales
Outside Sales Representative (Training Provided)
Platinum Supplemental InsuranceOswego, 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 | Oswego, IL, United States | Hybrid
This employer is a highly respected name in the supplemental insurance industry, known for its innovative AI-powered training and a supportive, people-first culture. They offer a unique opportunity for driven individuals to build a lucrative and rewarding career, regardless of prior experience. The company is committed to providing the tools, training, and support necessary for sales professionals to thrive and achieve financial success.
The Role
• Meet with business owners and families within your territory Monday through Thursday to educate them on supplemental insurance solutions.
• Utilize a proven 10-step sales system, enhanced by AI coaching, to guide prospects from interest to closing.
• Develop and nurture client relationships, focusing on understanding their needs and providing valuable protection.
• Collaborate with a supportive team, sharing best practices and contributing to a culture of continuous improvement.
• Travel within a designated territory Monday–Thursday, with evenings and weekends completely free.
What You'll Need
• A strong work ethic and intrinsic motivation to control and maximize your income.
• Excellent communication and interpersonal skills, with the ability to connect with diverse individuals.
• A coachable mindset, eager to learn and implement a proven sales system and AI-driven training.
• A willingness to travel within a territory Monday through Thursday for client meetings.
• Must be 18+ years of age.
What's On Offer
• Uncapped earning potential with typical first-year earnings exceeding $75,000, and opportunities for over $100,000.
• Opportunity for residual income through an ever-growing book of business.
• A consistent Monday-Thursday work schedule, ensuring every weekend is free.
• Comprehensive paid training, including licensing assistance and AI-powered coaching, with pay starting from day one in the field.
• Opportunities for career advancement into leadership roles through internal promotion.
• Eligibility for all-expenses-paid luxury travel incentives for top performers.
Apply via Haystack today!
Skills
Outside Sales
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