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Benefits Specialist / 12 Month (Grade 5) Position
Job in
Cheshire, New Haven County, Connecticut, 06410, USA
Listed on 2026-08-06
Listing for:
Cheshire High School
Contract
position Listed on 2026-08-06
Job specializations:
-
HR/Recruitment
HRIS Specialist, HR Generalist / Talent Management, Recruiter / Talent Acquisition, HR Manager
Job Description & How to Apply Below
Benefits Specialist - 12 Month Position
This is an excellent opportunity to join the Cheshire Public Schools as our Benefits Specialist and work with a successful leadership team in a high-performing K-12 school district. This key position in our organization reports to the Manager of Human Resources.
The Responsibilities:
- Administer all aspects of the various employee benefits programs including medical, dental, life insurance and retirement.
- Serve as the liaison between employees, insurance carriers and benefit vendors.
- Develop, oversee and promote the Health and Wellness Program to our employees.
- Provide insurance and benefits information to newly hired employees.
- Develop and manage the annual Employee Open Enrollment for our Benefit Programs.
- Assist the Payroll Supervisor in processing bi-weekly payroll, balancing benefit deductions and maintaining related records.
- Assist employees, retirees and spouses by providing general information, application and claim assistance on insurance programs.
- Maintain personnel records of all active and retired employees.
- Update central personnel files and adjust employee records for benefits coverage as needed.
- Budget for, track and analyze the programs offered and the costs associated with employee benefits.
- Keep abreast of new laws and assists in implement changes to remain in compliance with all regulatory and legal requirements.
- File and maintain Workers Compensation Claims.
- Perform other related duties, special projects and assignments, as needed, to ensure the efficient and effective functioning of the Payroll, Benefits and Human Resources.
Knowledge,
Skills and Abilities
Needed:
- Highly motivated and organized with the ability to effectively manage priorities and complete tasks and projects.
- Strong verbal, written and presentation skills required.
- A team player with the ability to establish and maintain cooperative and effective relationships with school employees at all levels.
- Able to interact proactively with a wide variety of audiences including administrators, department leaders, and vendors.
- Must have good analytical skills, adept with using technology and computer software including Munis and Excel.
- Ability to work independently and complete special projects and programs and to make sound judgment calls within assigned area of responsibility.
- Ability to maintain strict confidentiality with respect to information regarding students, employees, legal matters, financial information, collective bargaining, etc.
- Solid working knowledge of Benefits and Human Resources laws and regulations.
Qualifications:
- A combination of education and relevant experience to provide the required skills and knowledge for successful performance of the position is necessary.
- A minimum of three years of employee benefits experience including medical, dental, life insurance, retirement, health & wellness programs, new employee on-boarding and payroll processing knowledge is desired.
- A High School Diploma is required. A college degree or college-level course work in human resources, organizational management or business is definite plus.
- Prior experience working in a public school system or in a municipality is desired with business office experience a plus.
Compensation and Benefits:
In accordance with the Agreement Between Cheshire Board of Education and the Cheshire Educational Secretaries and Technicians United. Grade 5 Position, Starting Salary $36.50/hour. Excellent benefits are offered including medical, dental and a defined contribution retirement plan with an employer contribution match.
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