August 10, 2025 
Chicago, IL 
Full-time Job Descript
Location: Chicago, IL
Employment Type: Full-Time | Exempt
Experience Level: Mid Level (5–8 years)
Industry: Insurance
Reports To: Sales Team Leader
About the Role
On behalf of our client, HIB Recruitment Services is seeking a seasoned Sales Executive – Employee Benefits to lead growth in the Chicago market. This is a unique opportunity to be the anchor hire in a new market, helping to shape strategy, build relationships, and lay the foundation for future expansion.
The ideal candidate will have a proven track record in Employee Benefits sales, strong client relationship skills, and the ability to work independently while collaborating closely with leadership.
Key Responsibilities:
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Develop new client relationships through networking, referrals, and industry events
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Manage complex Employee Benefits accounts (100+ lives market) with the support of a dedicated service team
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Lead risk management strategies and recommend innovative insurance solutions
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Maintain and grow a book of business while meeting annual sales targets
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Identify cross-selling opportunities across additional lines of business
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Contribute to market strategy, recruiting, onboarding, and growth initiatives
Qualifications:
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6+ years of insurance agency sales experience in Employee Benefits
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Strong producer/closer track record with proven client retention
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Life & Health License (or ability to obtain within 60 days)
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Experience in middle-to-large group markets (100+ lives)
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Strong consultative sales skills and relationship-building ability
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Agency-side experience preferred (carrier-side considered)
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Based in or willing to relocate to Chicago, IL
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Willing to travel quarterly to HQ
