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Senior Account Executive, Employee Benefits in
Chicago, IL Job #CEW1906-04

Our client is a leading independent agency in the Midwest and one of the largest in the nation. They are currently seeking a dynamic individual to join their team as a Senior Account Executive for their Employee Benefits team. You will provide strategic planning and consulting advice to customers and prospects to include production of requests for proposal, coordinating vendor responses, analyzing RFP responses, and preparing client reports with recommendations.

Senior Account Executive, Employee Benefits Responsibilities

  • Develop implementation plans with clients to include coordinating and conducting enrollment meetings and training of client’s benefit personnel.
  • Review agreements and/or documents for accuracy.
  • Meet at least quarterly with clients to review large claims, monthly claims experience, and conduct on-site claims visits.
  • Develop financial projections for clients using actuarial modeling and deliver reports with commentary.
  • Supervise and interview potential candidates for team employment.

Senior Account Executive, Employee Benefits Requirements

  • 7-10 years of applicable experience in a brokerage/retail agency environment.
  • IL Life/Health license required.
  • Experience with self-funded medical plans and an agency management system preferred.
  • Additional designations such as RHU, REBC, and CEBS preferred.


Capstone Insurance Search Group is a search firm dedicated to the insurance industry. We work nationally with expertise that spans top executives, middle management and technical level positions. We can provide assistance with a variety of product lines to include Property and Casualty, Life, Health, Disability, Annuity and Pension. We will provide you with a service that is of the highest degree of confidentiality, professionalism and integrity.

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Who To Contact

Chris Winterboer, CPC, RHUPartner, Senior Search Consultant

(515) 987-0242 x453
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Chris started his career with Principal Financial Group in the group retirement division as a Benefits Counselor. From there he spent four years as an Employee Benefits Producer at Iowa’s largest independent agency before joining CSG in 2003. Chris works within three silos at CSG: group employee benefits, property & casualty (commercial and personal lines), and financial services/retirement planning. Chris is actively involved in advising and coaching candidates in their career development as well as serving as a consultant for his clients in helping them reach their goals. He continues to expand his national presence with his partnerships with retail agencies and brokers, carriers, MGUs & MGAs, advisory firms and consulting houses.

Chris is a graduate from Northwestern College where he was a collegiate golfer, and a graduate of both the Dale Carnegie Sales Advantage Program and Greater Des Moines Leadership Institute. Chris enjoys spending time with his wife and their three children, coaching his children’s sports teams, and being actively involved in the community through church and civic engagement.
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