About Careertakes

👉 Important disclosure: Careertakes is a third-party recruiting platform supporting this hiring process. If selected, you will be employed directly by our client, Sales — Health Insurance.

Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.

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Role Overview

This Confidential Client is hiring an Inside Sales Specialist to join a growing health insurance sales team in Chicago, IL. This is an entry-level, full-time inside sales role focused on inbound and warm outbound phone-based sales of health insurance plans. The company covers training and required insurance licensing costs. This position offers a base salary plus uncapped commission and benefits.

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Key Responsibilities

• Answer inbound calls and place warm outbound calls to customers to discuss and enroll them in health insurance plans.
• Guide consumers through plan selection, application, and enrollment processes.
• Learn and maintain product knowledge to act as a subject matter resource for health insurance offerings.
• Deliver an exceptional, compliant consumer experience on every call.
• Represent the Confidential Client’s brand professionally and courteously.
• Work in a competitive, performance-driven environment and meet or exceed sales targets.
• Use CRM and multi-screen computer setups to manage leads and applications.
• Complete required licensing and pass background checks as required by federal and state law.

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Qualifications

• Comfortable speaking with consumers on the phone and building rapport quickly.
• Strong communication and interpersonal skills.
• Basic computer proficiency; ability to use multiple screens and CRM tools.
• Self-motivated, coachable, and goal-oriented with a desire to grow into higher-level sales roles.
• Must be able to successfully complete insurance licensing and legal background requirements.
• Bachelor’s degree preferred but not required.
• Prior sales experience is a plus but not required — training provided.

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What the Confidential Client Provides

• Base salary plus uncapped commission (high earning potential).
• Company-paid training and required insurance licensing.
• Benefits including medical, dental, vision, 401(k), disability, and life insurance.
• Paid time off and performance-based incentives.
• Clear career progression and professional development opportunities.
• Supportive, high-energy team environment.

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Location & Employment Type

• Location: Chicago, IL (on-site)
• Employment type: FULL_TIME
• Note: This position requires authorization to work in the U.S. and the ability to complete licensing/background checks.

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Why Apply

This role is ideal for motivated, service-oriented people who want to start a career in sales within the health insurance industry. With company-paid licensing, structured training, a base salary and uncapped commission, many first-year agents earn competitive incomes while developing long-term career opportunities.

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Equal Opportunity & Hiring Transparency

Careertakes and our client are Equal Opportunity Employers committed to building a diverse and inclusive workforce. We prohibit discrimination or harassment of any kind. To support a fair and efficient hiring process, AI tools may be used to assist with application review or resume screening. These tools do not replace human decision-making. Final hiring decisions are made by people.

If you have questions about how your data is used, please contact us directly.