Associate Sales Representative
Listed on 2026-06-28
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Sales
Inside Sales, Sales Representative, Insurance Sales, Sales Associate/Assistant
Are you trying to break into sales and want a company that will actually train you how to succeed?
A reputable health insurance company in downtown Chicago is hiring motivated people for an Inside Sales Representative position. This is a great opportunity for recent college grads or anyone early in their career who wants to learn sales.
No insurance experience is needed. The company will pay for your insurance license, train you from the ground up both in sales and the industry, and pay you while you study and complete training.
This is a fully in-office role located in the Loop, with easy walkable access to the El and Metra.
Why is this opportunity so great?
- $42,000 base salary plus uncapped commissions
- Most people earn between $55,000 and $65,000 in their 1st year
- No cold calling. You’ll either answer calls from people actively looking for health insurance information or follow up with people the company has already spoken with who haven’t made a decision yet.
- Paid training and licensing
- Fun, competitive office environment
- Great downtown location whether you live in the city or suburbs
- Full benefits package plus commuter benefits
You’ll speak with people who are already looking into health insurance and want to learn more.
You’ll help answer questions, explain plan options, and guide people through the enrollment process.
This is a phone-based sales role, so you should be comfortable spending the majority of the day talking with people and building relationships.
What They’re Looking For- Someone motivated, competitive, and eager to learn
- Comfortable talking to people all day
- Ability to work in a fast-paced environment
- Previous sales or customer service experience is helpful, but not required
- Basic computer and multitasking skills
- Ability to pass licensing and background requirements
- Bachelor’s degree is a plus, but not required
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