Benefits & Leave Specialist: Compliance & Support

24 Seven; Bellevue (WA); On-site; USD 41,000 - 83,000; Full time

Job summary

24 Seven is 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. You will administer leaves, answer questions on eligibility and plan options, maintain records in HRIS, assist open

Qualifications

• 2+ years in benefits or leave administration or HR operations roles.
• Knowledge of U.S. benefits and leave regulations (ERISA, ACA, HIPAA, FMLA).
• Experience managing leave requests and employee communications.

Responsibilities

• Administer leave-of-absence requests from intake through return-to-work coordination, ensuring policy compliance.
• Respond to questions on benefits eligibility, plan options, claims, enrollment, and leaves.
• Manage benefits support requests with accuracy and empathy, ensuring follow-through.
• Maintain benefits eligibility records, documentation, and data in HR/benefits systems.
• Support open enrollment activities, including communications, materials, reporting, and vendor coordination.
• Coordinate with benefits vendors to resolve claims issues, data discrepancies, and system concerns.
• Prepare benefits reports, reconciliations, and compliance documentation.
• Assist with compliance activities related to ERISA, ACA, HIPAA, FMLA, and regulations.
• Support benefits program implementations, data validation, testing, and communications.
• Contribute to HR operations initiatives and special projects.

Skills

Benefits administration

Leave-of-absence administration

HR operations

HRIS

Vendor portals

Communication skills

Attention to detail

Tools

HRIS systems

Benefits platforms

Vendor portals

Job description

24 Seven is 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. You will administer leaves, answer questions on eligibility and plan options, maintain records in HRIS, assist open