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10/31/2026

Chicago Health & Benefits Office Business Leader

Job Description

Summary of Role 

The Chicago Health & Benefits (H&B) OBL is a key member of the Midwest Region H&B leadership team. In this role, you will have ultimate accountability for the H&B business and team in the market: the role’s success metrics are tied to growing revenue and talent. This includes revenue growth, direct expense management, and profitability; colleague attraction, development and engagement; and client and colleague retention. The OBL is effectively the Growth Leader of the market, responsible for building and executing the growth plan to meet/exceed the expected results. The OBL will be responsible for building the WTW brand externally, and leading key new client pursuits

The role will report to the Health & Benefits Midwest Region Leader (RL).

The Role

  • Build and execute the local market business strategy to achieve growth, retention, staffing, and profitability goals.
  • Manage the local H&B new-business pipeline and sales opportunities in partnership with Producers, Senior Sellers, Lead Relationship Managers, Region Leaders, and Specialist Community Leaders
  • Strengthen WTW’s brand through engagement in local events, hosting marketing events, and talent networking
  • Develop strategies to retain and grow profitable client relationships, including cross-LOB opportunities
  • Lead recruiting and talent management for the market and people-manage senior colleagues
  • Develop the market talent pipeline and strategic staffing plans, including deployment, performance management, development, and appropriate leverage models
  • Foster colleague engagement across the market
  • Serve as a player-coach” by mentoring colleagues in business development and client management capabilities 
  • Oversee the market’s operational effectiveness
  • Maintain effective governance, controls, and compliance in support of corporate strategy and goals
  • Champion market adherence to the H&B Excellence Model
  • Partner with the Region Leader, Geography Leaders, and other OBLs to execute regional H&B priorities and initiatives
  • Serve on the Regional H&B and local Geography leadership teams

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WTW
WTW

Where we are

We have colleagues all around the world, working remotely or in our offices. Together, we make a difference for clients in over 140 countries and markets, from the Middle East to Latin America, from Manila to New York.