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Benefits and Employment Specialist

Orange Southwest School District
Randolph, VT Full Time
POSTED ON 10/9/2025 CLOSED ON 1/16/2026

What are the responsibilities and job description for the Benefits and Employment Specialist position at Orange Southwest School District?

Orange Southwest School District Job Title: Benefits and Employment Specialist Reports To: Superintendent and Business Manager FLSA Status: Non-Exempt / Full-Time Location: Central Office Date: 7 May 2025 Position Summary: The Benefits and Employment Specialist plays a vital role in supporting the human resources operations of the Orange Southwest School District. This position is responsible for coordinating the end-to-end employment process, including job postings, onboarding, benefits support, and employee exit procedures. The Specialist ensures compliance with all federal and state employment regulations and provides high-quality customer service to staff across the district. This position requires a strong communicator who is organized, detail-oriented, tech-savvy, and able to collaborate effectively across departments. The ideal candidate will maintain a positive, solutions-focused demeanor while balancing multiple responsibilities and maintaining confidentiality. •The district is willing to provide training for candidates who demonstrate strong potential ________________________________________ Key Responsibilities: Recruitment & Hiring Support •Collaborate with hiring managers to create, review, and post job vacancies on approved platforms. •Track postings and coordinate communication throughout the hiring process to ensure a smooth candidate experience. •Prepare and issue employment contracts in alignment with board-approved templates, master agreements, and district hiring practices. Onboarding & Orientation •Coordinate the completion of all required new hire paperwork and ensure compliance with district, state, and federal requirements. •Guide new employees through the onboarding process, including orientation materials, benefit enrollment, and technology access. Benefits Administration •Serve as a point of contact for employee questions related to benefits as outlined in applicable master agreements, working collaboratively with association representatives to ensure employees receive clear, accurate, and timely information. •Assist employees in navigating benefit options, enrollment, and updates in coordination with both district leadership and union representatives. •Facilitate the open enrollment process by providing direct support to staff, including visiting each school site to ensure all employees have access to information regarding their potential benefit selections. •Coordinate benefits communications and updates; assist staff in understanding and accessing their benefit options. FMLA & Leave Coordination •Manage and track Family and Medical Leave Act (FMLA) requests and other applicable leaves, in close collaboration with the Superintendent, Business Manager, and school administrators to ensure compliance, consistency, and effective staffing support. •Ensure timely and accurate documentation, communication, and compliance with legal and contractual obligations. Workers Compensation •Coordinate and process Workers’ Compensation claims in collaboration with insurance providers and district leadership. •Coordinate Workers’ Compensation claims in partnership with VSBIT, the district’s insurance carrier, serving as a liaison between injured employees, school leaders, and VSBIT to ensure timely communication and proper documentation. VSBIT will manage the claims process directly, with district support focused on internal coordination and compliance. •Maintain records and ensure compliance with reporting requirements. Employee Exit & Offboarding •Coordinate the offboarding process to ensure employees complete final paperwork, return district property, and understand benefit transitions. •Maintain compliance with exit documentation requirements at both the state and federal levels. •Maintain communication with necessary departments and association representatives as needed to ensure employee transitions are handled with clarity and fairness. Records & Compliance •Maintain accurate and confidential personnel records in compliance with district policies and legal requirements. •Take a lead role in improving the accuracy and integrity of employee data within the district’s employee management system (Tyler), including regular audits, data clean-up, and collaboration with the Business Office and IT teams to ensure up-to-date and consistent records. •Support audits, internal reporting, and data requests related to employment, benefits, and compliance Minimum Qualifications: •The district is willing to provide training for candidates who demonstrate strong potential •At least two years of office experience required, experience in a school or public sector setting a plus •Associate’s degree in human resources, Business Administration, or a related field preferred •Knowledge of employment laws and regulations, including FMLA, is preferred •Experience with HR or applicant tracking software preferred Required Skills & Attributes: •Excellent verbal and written communication skills •Strong technology skills and comfort working with HRIS systems, Google Workspace, and electronic record •Highly organized with strong attention to detail •Proven ability to collaborate and build positive relationships with colleagues across roles •Demonstrated problem-solving abilities and the capacity to manage sensitive matters with discretion •A collegial and professional demeanor with a commitment to customer service •Experience working with employee management systems (e.g., Tyler or similar HRIS platforms); ability to troubleshoot and improve data accuracy ________________________________________ Work Environment: This position is based at the Central Office and operates in a fast-paced, professional environment. Occasional travel to school sites may be required. ________________________________________ To Apply: Please submit a cover letter, resume, and three references through [SchoolSpring or District Application Portal]. Salary range dependent on experience $20-$25/hour OSSD Equal Employment Opportunity Statement We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. We encourage all qualified applicants to apply.

Salary : $20 - $25

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