Spencer James Group provides dedicated insurance recruiter services serving Chicago and the broader Midwest region. Organizations seeking an insurance recruiter with deep knowledge of the Windy City’s market dynamics turn to the firm for access to major carriers, regional insurers and innovative agencies throughout Illinois.

Chicago boasts a rich insurance heritage dating back to 1834 when Aetna established its first Midwestern agency here. Today, the metropolitan area hosts major operations from CNA Financial, which maintains its headquarters downtown, alongside Allstate in Northbrook and Zurich North America. The city serves as the insurance capital of the Midwest, with over 50,000 professionals employed across carriers, brokerages and related services.

The Chicago insurance market spans property and casualty, employee benefits and specialty lines including agricultural and transportation coverage. Companies such as Arthur J. Gallagher, one of the world’s largest insurance brokers, maintain their global headquarters in the Chicago suburbs. The city’s central location makes it ideal for regional underwriting hubs and claims operations serving multiple states.

Spencer James Group’s executive search practice focuses on placing senior leaders and specialized professionals throughout Chicagoland. As a committed headhunter, the firm understands the nuances of Chicago’s insurance culture, from Loop high-rises to suburban corporate campuses. Insurance executive compensation here typically ranges from $130,000 to $170,000 for director-level positions, with strong growth opportunities in data analytics, InsurTech and risk management consulting roles.

You're in Good Company

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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.