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Benefits Specialist ​/ 12 Month (Grade 5) Position

Job in Cheshire, New Haven County, Connecticut, 06410, USA
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
Salary/Wage Range or Industry Benchmark: 36.5 USD Hourly USD 36.50 HOUR
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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