Director of Insurance and Group Benefits

Director of Insurance and Group Benefits JobID: 3100

Position Type:

Administrative

Date Posted:

5/28/2026

Location:

Administration Center

Date Available:

07/01/2026

Closing Date:

06/10/2026

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Township High School District 211

Director of Insurance and Group Benefits

(Reports to Chief Operating Officer)

The Director of Insurance and Group Benefits will embody the district mission, serving the needs of our diverse community by providing strategic leadership and stewardship of employee insurance, retirement, and group benefits programs that support the recruitment, retention, and well-being of a highly qualified workforce, while upholding our values of communication and accountability, equity and inclusion, financial integrity, innovative learning, and safety, wellness, and respect.

The Director of Insurance and Group Benefits provides strategic direction, oversight, and continuous improvement of the district's comprehensive employee insurance, retirement, and risk management programs. The position is responsible for ensuring that employee and retiree benefits are competitive, fiscally responsible, legally compliant, and responsive to the needs of the district's workforce while supporting long-term operational and financial stability.

Position Purpose:

The Director of Insurance and Group Benefits leads the administration, implementation, and evaluation of districtwide insurance and employee benefit programs, including health, dental, vision, life, disability, workers' compensation, liability, property, cyber, voluntary insurance, and retirement-related benefits. The Director oversees benefits administration, open enrollment, pension coordination, vendor partnerships, compliance monitoring, employee communications, and wellness initiatives to ensure alignment with district priorities and all applicable federal and state laws and regulations.

Serving a high school district of approximately 12,300 students and a large employee workforce, the Director collaborates with district administrators, employee groups, union insurance committees, insurance providers, retirement systems, consultants, and third-party administrators to ensure that benefit and insurance programs are employee-centered, financially sustainable, operationally efficient, and aligned with the district's mission and strategic plan. The position also serves as a key resource for employees and retirees regarding retirement planning, pension systems, claims resolution, and benefits education.

Qualifications

• Bachelor degree in Human Resources, Business Administration, Insurance, Finance or a related field; Chief School Business Official endorsement preferred
• Minimum of five years of progressively responsible experience administering employee benefits programs, preferably within a public school district
• Demonstrated experience in the management of an employee benefits program including health, dental, vision, life, disability and voluntary benefit plans
• Extensive knowledge of Illinois public pension systems, including the Illinois Teachers' Retirement System (TRS) and Illinois Municipal Retirement Fund (IMRF) preferred
• Thorough knowledge of federal and state laws and regulations governing employee benefits administration, including HIPAA, ACA, COBRA, FMLA, IRS regulations, and applicable Illinois School Code provisions preferred
• Experience managing employee benefit open enrollment processes, benefits communication strategies, and vendor relationships
• Advanced proficiency in Microsoft Excel, database systems, and HRIS/payroll systems; experience with Infinite Visions HR/Payroll System preferred
• Demonstrates effective interpersonal, presentation, and communication skills
• Self-directed professional with exceptional attention to detail and the ability to manage multiple priorities with minimal supervision
• Demonstrated ability to analyze complex benefits data, retirement projections, claims trends, and financial reports to support strategic decision-making
• Ability to maintain confidentiality and exercise sound judgment in handling sensitive employee and benefits information

Essential Functions:

• Directs and administers the District's comprehensive employee insurance and benefits programs including health, dental, vision, life, long-term disability, workers' compensation, liability, property, crime, cyber, and voluntary insurance programs
• Oversees all aspects of employee and retiree benefits administration, including plan implementation, enrollment, eligibility, claims coordination, premium processing, and employee communication
• Leads the District's annual insurance open enrollment process, including system configuration, employee education, communication materials, and vendor coordination
• Serves as the District's authorized agent and primary liaison with the Illinois Municipal Retirement Fund (IMRF) and collaborates with the Illinois Teachers' Retirement System (TRS) regarding retirement reporting, compliance, and employee retirement counseling
• Provides retirement counseling and pension guidance to employees and retirees regarding TRS and IMRF benefits, retirement eligibility, timelines, and post-employment insurance information
• Prepares and analyzes retirement projections and benefits cost analyses in collaboration with the Chief Operating Officer and Director of Human Resources
• Assists the Chief Operating Officer with oversight of risk management initiatives and coordination of liability claims filed against the District
• Evaluates insurance brokers, consultants, carriers, and third-party administrators to ensure cost-effective and high-quality benefit services
• Assists in the preparation and presentation of insurance and employee benefits reports for administration, the Board of Education, and union insurance committee meetings
• Ensures District compliance with all applicable federal and state laws, regulations, and reporting requirements related to employee benefits and retirement systems
• Serves as the District's HIPAA Privacy Compliance Officer and oversees compliance related to confidential employee health and benefits information
• Participates in cooperative risk management and insurance consortium meetings and maintains collaborative relationships with external agencies and professional organizations
• Directs employee and retiree benefits enrollment and premium payment processes and supervises staff responsible for benefit transaction processing and record maintenance
• Develops recommendations to optimize District resources and improve the efficiency, effectiveness, and competitiveness of employee benefit programs
• Assists employees and retirees with benefit concerns, claims resolution, retirement planning questions, and pension-related inquiries
• Monitors pending legislation, regulatory updates, and industry trends impacting employee benefits, pensions, and school district compliance obligations
• Maintains expertise in employee benefits administration and provides strategic recommendations regarding plan design, compliance, and emerging benefit trends
• Coordinates and facilitates meetings with union insurance and wellness committees and promotes employee wellness initiatives throughout the District
• Develops and delivers effective employee communication and educational materials regarding insurance benefits, retirement systems, wellness programs, and benefit changes
• Establishes and maintains positive working relationships with employees, retirees, union representatives, insurance providers, and community stakeholders representing diverse backgrounds and perspectives
• Supervises designated support staff and evaluates performance in accordance with District procedures
• Performs other duties as assigned by the Chief Operating Officer

Working Conditions and Terms:

• Typical administrative hours; 12-months per year; attendance at periodic meetings required
• Travel between district/school sites; occasional state/national travel for conferences
• Compensation, benefits, and contract terms in accordance with Administrator Compensation and Benefit Package

Application Question:

Please explain how your professional experience, knowledge of employee insurance and retirement systems, and leadership abilities prepare you to successfully serve as the Director of Insurance and Group Benefits in a large public school district. Include examples of your experience with employee benefits administration, compliance, retirement counseling, financial analysis, and collaboration with employees, unions, and external partners.

Application

Interested candidates must complete an online application (https://adc.d211.org/employment)

Salary Range

$118,105-140,000

Candidates may contact:

Lauren Hummel, Chief Operating Officer, at

LHummel@d211.org