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Chicago Health & Benefits Office Business Leader

WTW

Chicago, IL · HybridJob$220–330K/yrSeen todaySeen in employer's feed today

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At a glance

Compensation
$220–330K/yr
Location
Chicago, ILHybrid
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

The Chicago Health & Benefits Office Business Leader is accountable for the local H&B business and team, with success measured by revenue growth, profitability, talent development, and client and colleague retention. Reporting to the Health & Benefits Midwest Region Leader, the role builds and executes the market growth plan, strengthens WTW’s external brand, leads new-client pursuits, and contributes to regional and local leadership priorities.

Skills & qualifications

RequiredNice to have

Skills

Team LeadershipTeam DevelopmentTalent Pipeline ManagementRevenue GenerationHealth and Benefits DesignClient Relationship ManagementStrategic PlanningRelationship BuildingCollaborationWritten CommunicationOral CommunicationHealthcare TrendsBenefits TrendsMarket KnowledgeKPI ManagementAdaptabilityInterpersonal SkillsBusiness AcumenOrganizational SkillsCreative Thinking

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
Paid Time Off
Parental Leave
401(k) Match

Full job description

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

Qualifications

The Requirements

  • Strong experience in leading and developing teams

  • Strong experience in developing and managing an active talent pipeline `

  • Proven track record of individual success in generating new revenue with new or existing clients as they relate to health and benefits services

  • Knowledge and expertise in health and benefits design and management

  • Track record of success in managing and expanding client relationships

  • Lead strategic efforts that define new opportunities for achieving competitive advantage

  • Proven ability to establish relationships and work collaboratively with team members across the organization and at all levels, to effectively deliver on client needs across all market segments

  • An executive presence with polished and well developed written and oral communication skills

  • Interest and aptitude in keeping abreast of latest developments in health care and benefit trends and contributing to the development of new tools and approaches

  • In-depth knowledge of the market, H&B NA capabilities, and broader WTW offerings

  • Results-oriented with ability to effectively manage to KPIs

  • Comfortable with change and uncertainty and able to work through ambiguity

  • Excellent leadership, interpersonal, and communication skills.

  • Strong business acumen, strategic planning, organizational, and creative thinking skills

This position will remain posted for a minimum of three business days from the date posted or until a sufficient/appropriate candidate slate has been identified.

Compensation

The base salary compensation range being offered for this role is $220,000– $330,000 USD per year. This role is also eligible for an annual short-term incentive bonus.

Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

  • Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)

  • Leave Benefits: Paid Holidays, Annual Paid Time Off (includes paid state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave), Paid Time Off (https://cdn-static.findly.com/wp-content/uploads/sites/1862/2023/01/31091722/Washington-State-Time-Off.pdf) ( Washington State only )

  • Retirement Benefits: Contributory Pension Plan and Savings Plan (401k).

At WTW, we trust you to know your work and the people, tools and environment you need to be successful. The majority of our colleagues work in a ”hybrid” style, with a mix of remote, in-person and in- office interactions dependent on the needs of the team, role and clients. Our flexibility is rooted in trust and “hybrid” is not a one-size-fits-all solution.

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications qualifications/experience, performance in the role and potential for revenue generation (Producer roles only)

We understand flexibility is key to supporting an inclusive and diverse workforce and so we encourage requests for all types of flexible working as well as location-based arrangements. Please speak to your recruiter to discuss more.

Compensation and Benefits

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that base salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation (Producer roles only).

Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)

Leave Benefits: Paid Holidays, Annual Paid Time Off (includes paid state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave), Paid Time Off ( Washington State or remote only )

Retirement Benefits: Contributory Pension Plan and Savings Plan (401k).

We’re committed to equal employment opportunity and provide application, interview and workplace adjustments and accommodations to all applicants. If you foresee any barriers, from the application process through to joining WTW, please email [email protected].

This position will remain posted for a minimum of three business days from the date posted or until sufficient/appropriate candidate slate has been identified.

EOE, including disability/vets

Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records.

How this job compares

Set against the 465 open Sales Leader jobs on Olive Jobs, counted October 27, 2026.

Pay
  • This posting$220–330K/yr
  • US median$163–253K/yr296 salary ranges

This range's midpoint, $275K, is 31% above the US median midpoint ($210K) — in the middle half of Sales Leader salary ranges across the US.

Openings
Olive Jobs lists 18 open Sales Leader jobs in Illinois and 465 across the US. 9% of them nationwide are listed as remote or flexible.
Hiring the most across the US
Experience
Sales Leader postings that state a minimum ask for 8 years of experience at the median; the middle half ask for 5 to 10 years (346 postings).
Education
130 of the 465 open Sales Leader jobs (28%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on October 27, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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