Outside Sales Representative

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

This employer is a leader in the supplemental insurance industry, renowned for its innovative AI-powered training and commitment to employee growth. They offer a unique opportunity for driven individuals to build a rewarding, high-earning career with a proven system and dedicated support, regardless of prior experience. The company fosters a positive, people-first culture that prioritizes work-life balance and recognizes top performance.

The Role

• Engage directly with business owners and families to educate them on supplemental insurance solutions.
• Utilize a proven 10-step sales process with AI-driven coaching to guide prospects and close deals.
• Develop and manage client relationships within an assigned territory.
• Collaborate with a supportive team to share best practices and achieve collective success.
• Travel within the territory Monday through Thursday, with evenings and weekends free.

What You'll Need

• Strong communication and interpersonal skills.
• A self-starter mentality with a willingness to follow a structured system and learn.
• Comfort with technology, including AI-powered training tools.
• Ability to travel for work commitments Monday through Thursday.
• A desire to control income potential and drive performance.

What's On Offer

• Uncapped earning potential with typical first-year incomes of $75,000+, plus residual renewal income and performance bonuses.
• A consistent four-day workweek (Monday-Thursday) ensuring every weekend is free.
• Comprehensive training, including licensing assistance, paid initial training, and ongoing AI-powered coaching.
• Opportunities for career advancement and promotion from within the organization.
• All-expenses-paid travel incentives for top performers.

Apply via Haystack today!