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Entry-Level Benefits Associate

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Onsite

Entry-Level Benefits Associate

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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