Identifying qualified sales professionals for employee benefits brokerages and carriers across the Chicago metropolitan area is the primary focus of a specialized insurance recruiter serving this market. The metro region maintains approximately 3.8 million total nonfarm jobs with healthcare and social assistance leading employment growth, adding over 16,000 positions in private education and health services in recent months. Finance and insurance represent the third-highest employment concentration among major U.S. metros, supporting sustained demand for group health, disability and life insurance distribution talent.

Chicago’s economic base includes transportation and warehousing operations that benefit from the city’s position as a national logistics hub. Construction employment added 4,500 jobs in the metropolitan corridor through mid-2025. Healthcare systems across the region employ hundreds of thousands of workers who require group medical, dental and vision coverage along with ancillary/voluntary benefits like accident and critical illness products. These employer segments create ongoing needs for benefits advisors who understand self-funded and fully insured plan structures.

Executive search capabilities address senior-level openings for regional vice presidents and agency principals who can navigate relationships with mid-market and large employers. A headhunter with expertise in the employee benefits sector identifies candidates who possess established broker networks throughout Chicagoland and surrounding areas. Service roles including enrollment coordinators and account managers support the administrative complexity of group coverage for employers in finance, healthcare and logistics.

The metropolitan area’s concentration of insurance carriers and national brokerage operations generates consistent demand for both producers and client-facing service professionals. Leadership positions require familiarity with the competitive dynamics of a market where transportation and distribution employers maintain large covered populations alongside professional services organizations.

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Partner With Us on Your Next Chicago-Based Search

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Why Choose The Spencer James Group For Your Chicago Insurance Role

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We save time

True headhunting is time-consuming. Our insurance staffing services dedicate the resources to finding a great solution for your search, so you don't have to.

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We know the talent you want

We have over 30,000 people in our candidate database and over 25,000 direct connects on LinkedIn. We'll connect you with the best insurance talent in the industry.

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We build real relationships

Candidates answer our phone calls because they already know and trust us. Our insurance recruiters excel at building relationships and securing top talent.

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We guarantee quality

Working with Spencer James is an investment in your future success. We guarantee our candidates will deliver. If not, we’ll replace them at no additional cost.

Typical Roles We Fill in Chicago

Broker

  • Account Executive
  • Account Manager
  • Benefits Consultant
  • Client Service Executive
  • Client Service Manager
  • Consultant
  • Producer
  • Practice Leader
  • Team Leader
  • Unit Manager
  • Vice President
  • Voluntary Specialist

Carrier

  • Account Manager
  • Employee Benefits Representative
  • Group Representative
  • Head of Sales
  • Regional Account Manager
  • Regional Director
  • Regional Sales Executive
  • Regional Service Manager
  • Regional Vice President
  • Sales Consultant
  • Sales Director
  • Sales Manager
  • Sales Rep
  • Senior Account Manager
  • Service Director
  • Specialty Sales Executive
  • Stop Loss Sales Rep
  • Vice President
  • Voluntary Sales Executive
  • Worksite Sales Rep

See What Our Clients Say About The Spencer James Group

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John Kirke

President | BevCap Management LLC

Steve and The Spencer James Group are exceptional, value-creating business partners in the world of employee benefits consulting and brokerage talent acquisition. Steve helped our Employee Benefits division recruit and land incredible, top-tier client-facing talent that accelerated a critical market for our team. Steve invested in our business, deeply knew our culture and was our first call for talent needs.
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Ron Altbaum

Regional Vice President of Distribution | MGIS

I’ve worked with the Spencer James Group for over three years and their ability to pre-screen and deliver top-notch candidates is unrivaled. They bring integrity and a long-term approach so often ignored in the industry. The candidates they have brought us have exceeded our expectations without surprises. The Spencer James Group not only has the candidates – they ensure the right fit.