Benefits & Leave Specialist

Employment Type: Freelance

We are seeking a detail-oriented Benefits & Leave Specialist to support the administration of U.S. employee benefits and leave programs for a growing organization in the work management software industry. This freelance role is ideal for someone who combines strong benefits knowledge with an employee-first approach, ensuring accurate, compliant, and responsive support.

What You’ll Do

• Administer leave-of-absence requests from intake through return-to-work coordination, ensuring timely communication and policy compliance.
• Respond to employee questions regarding benefit eligibility, plan options, claims, enrollment, and leave programs.
• Manage and resolve benefits support requests with accuracy, empathy, and consistent follow-through.
• Maintain employee benefits eligibility records, documentation, and data within HR and benefits administration systems.
• Support open enrollment activities, including employee communications, enrollment materials, reporting, and vendor coordination.
• Partner with benefits vendors to resolve claims issues, participant questions, data discrepancies, and system-related concerns.
• Prepare benefits reports, reconciliations, employee summaries, and compliance-related documentation.
• Assist with compliance activities related to ERISA, ACA, HIPAA, FMLA, and other applicable federal and state regulations.
• Support benefits program implementations, including data validation, testing, employee communications, and process documentation.
• Contribute to special projects and broader HR operations initiatives as needed.

What You Bring

• 2+ years of experience in benefits administration, leave-of-absence administration, or a related HR operations role.
• Working knowledge of U.S. benefits and leave regulations, including ERISA, ACA, HIPAA, and FMLA.
• Experience managing leave requests, supporting documentation, and employee communications.
• Comfort working with HRIS, benefits administration platforms, and vendor portals.
• Strong organizational skills and exceptional attention to detail.
• Clear, professional communication skills and the ability to explain benefits information in an approachable manner.
• Ability to manage multiple priorities, meet deadlines, and maintain a high degree of accuracy.
• A collaborative approach to partnering with employees, vendors, HR colleagues, and internal stakeholders.
• Sound judgment, strong problem-solving skills, and comfort escalating issues when appropriate.
• A demonstrated commitment to confidentiality and the responsible handling of sensitive employee information.