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Benefits Specialist ​/ 12 Month (Grade 5) Position

Job in Cheshire, New Haven County, Connecticut, 06410, USA
Listing for: Cheshire Public Schools
Contract position
Listed on 2026-08-09
Job specializations:
  • HR/Recruitment
    HR Generalist / Talent Management, HRIS Specialist, 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.
Additional Duties

Perform other related duties, special projects and assignments, as needed, to ensure the efficient and effective functioning of the Payroll, Benefits and Human Resources.

Note:

The above description is illustrative of tasks and responsibilities. It is not meant to be all inclusive of every task or responsibility.

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.

Cheshire Public Schools - A Great Place to Work

Visit our website at https://(Use the "Apply for this Job" box below). to learn more about our award winning health and wellness benefits and why we are a great place to work.

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