Insurance Jobs in Chicago, IL

Summary
A captive is a licensed insurance company that is established to enable an entity to manage, or in the case of a group captive, multiple entities to manage and finance their risk more efficiently. The role of the Captives & Insurance Management Solutions Practice is to then manage the captive once an entity has established it. The Captive Account Manager will work assisting the team in producing accurate and pertinent financial, insurance and accounting information on a timely basis to enable the Captive Boards to make informed decisions. This will include liaising with the parent company, insurance regulator, directors, and service providers in respect of the above.

This position is a senior client-facing role responsible for directly supporting commercial Property and Casualty Insurance client relationship management efforts and coordinating all service activity at the program level. The senior Account Manager/Financial Analyst is a key member of the client service team responsible for facilitating the delivery of program level strategy and providing program consultation to clients.

Note: visa employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity.

The Role
Serve as the primary financial reporting liaison for assigned captive clients, providing technical expertise and oversight across member escrow accounts, loss billing, captive financial statements, and member equity reporting. This role is responsible for managing client financial reporting, supporting underwriting and renewal activities, maintaining strong client relationships, and identifying opportunities for organic growth within an existing portfolio.

Key Responsibilities

Client Financial Reporting & Oversight

Act as the subject matter expert and escalation point for financial reporting matters, including:

• Member escrow accounts
• Loss billing reconciliations
• Captive financial statements
• Member equity statements

Responsibilities include:

• Preparing and reconciling monthly financial data with the Domicile Manager (DM)
• Preparing, reconciling, and analyzing loss billing activity with carriers and the DM
• Preparing, reconciling, and analyzing member escrow statements semi-annually
• Preparing, reconciling, and analyzing member equity statements annually
• Preparing, reconciling, and analyzing collateral requirements for insureds and carriers

Client Portfolio & Revenue Management

• Manage and retain revenue within an assigned client portfolio
• Identify and support organic growth opportunities
• Deliver proactive client service and relationship management

Pre-Renewal Strategy & Planning

• Lead internal renewal strategy meetings, including:
  • Program performance reviews
  • Expiring exposure analysis
  • Client service agreement reviews
  • Service planning and delivery discussions
• Partner with Producers and Account Executives to facilitate external client strategy meetings
• Document meeting outcomes, action items, and next steps

Underwriting & Program Management

• Collaborate with broker partners and insureds to gather underwriting information
• Review client exposure updates and provide coverage recommendations
• Monitor exposure trends and risk transfer pricing across assigned programs
• Develop underwriting materials and exhibits for annual board meetings as needed
• Present underwriting and program information to management and captive boards of directors
• Develop program-level proposal content and document coverage decisions and changes
• Process bind orders and ensure timely delivery of binders and coverage documentation
• Coordinate premium invoicing, collection, and premium cession activities
• Monitor policy issuance and endorsement processing while serving as liaison between brokers and carriers

Client Service & Administration

• Coordinate and prepare materials for client meetings and presentations
• Present information to client boards and committees as required
• Respond promptly to client inquiries and deliver best-in-class client service
• 20% travel involved

Relationships

Internal Partnerships:

• Collaborate with internal teams to ensure consistency of processes and service delivery
• Coordinate with cross-functional departments to support client and program objectives

External Relationships:

• Build and maintain strong relationships with:
  • Clients
  • Broker partners
  • Insurance carriers
  • Third-party service providers

Success Measures

• Accurate and timely financial reporting
• Effective management of client programs and renewals
• Strong client retention and satisfaction
• Growth within the existing client portfolio
• Successful collaboration with internal and external stakeholders

The Requirements

Education:

• Bachelor's degree in Accounting, Finance, or a related field

Experience:

• Minimum of 5 years of experience in accounting, financial analysis, or a related discipline
• Experience in insurance, captive management, or insurance-related financial transactions is preferred
• Interest in learning insurance operations and risk financing concepts

Technical Skills:

• Advanced computer proficiency, including financial analysis and reporting tools
• Strong analytical and problem-solving skills with attention to detail

Client Service & Communication:

• Strong client service orientation with the ability to build and maintain professional relationships
• Comfortable interacting directly with clients and external stakeholders
• Excellent interpersonal, verbal, and written communication skills
• Ability to explain financial information clearly to both technical and non-technical audiences

Professional Competencies:

• Strong organizational and time management skills
• Ability to manage multiple priorities and meet deadlines in a fast-paced environment
• Collaborative team player with the ability to work effectively across functions

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.

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 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).

Compensation

The base salary compensation range being offered for this role is $110,000.00-$150,000.00 USD annually.

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 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 (only included for Washington roles)
• Retirement Benefits: Qualified contributory pension plan (if eligible) and 401(k) plan with annual nonelective company contribution. Non-qualified retirement plans available to senior level colleagues who satisfy the plans’ eligibility requirements.

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.

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.

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.

EOE, including disability/vets