HEALTH WITH HENRY INSURANCE
Entry-Level Benefits Associate
1 month ago
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Important information
Contract type:
Permanent
Salary:
$65,000 – $90,000 / year
Location:
Chicago, IL, USA
Work mode:
Onsite
Published on:
28 September 2026
What they need
CANDIDATE-FACING JOB DESCRIPTION
You may be a strong fit for this role if you can say yes to most of these:
- I am comfortable starting conversations with new people.
- I can listen before I start explaining.
- I want a role where training is provided but effort is still expected.
- I can follow a process and keep accurate notes.
- I am motivated by goals and performance.
- I am willing to learn insurance products and licensing requirements.
- I want a professional path with room to advance.
The Entry-Level Benefits Associate works with prospective clients who are reviewing insurance and benefit options. You will learn how to identify client needs, explain available coverage, help clients understand next steps, support applications, maintain documentation, and follow up. The position also includes sales activity, so candidates should be comfortable working toward production goals.
You do not need previous insurance experience. Paid training, coaching, and licensing assistance may be available. Experience in customer service, retail, hospitality, restaurants, banking, call centers, automotive sales, wireless, fitness, healthcare, or other people-facing work can transfer well.
What the opportunity includes:
Paid training
Weekly pay
Performance-based bonuses
Career-development opportunities
Leadership-development opportunities
Flexible scheduling
Full-time, Monday-Friday schedule
Pay range: $65,000-$90,000 per year.
Work location: In person in Chicago.
If you are looking for your first professional insurance opportunity and want your progress to be tied to what you learn and produce, apply to be considered.
Pay: $65,000.00 - $90,000.00 per year
Work Location: In person
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