Senior Benefits Contractor

Position: Benefits Contractor – Health & Welfare Compliance

Location: Waltham, MA (Onsite minimum 3 days/week)

Reporting To: Senior HR Leader

Employment Type: Contract

Role Overview

We are seeking an experienced Benefits Contractor to support the administration and compliance of health and welfare benefit programs. This role plays a critical part in ensuring regulatory adherence, managing employee lifecycle benefit transactions, and supporting cross-functional HR operations. The ideal candidate will have deep expertise in benefits compliance, including ACA reporting, and experience working with Oracle HRMS.

Key Responsibilities

Compliance & Regulatory Oversight

• Administer and ensure compliance with health and welfare benefit programs
• Maintain up-to-date knowledge of ERISA, HIPAA, ACA, and state-specific regulations
• Execute compliance-related activities including 5500 filings, ACA reporting, IRC testing, and tax-related benefit implications
• Manage additional government filings, plan audits, and other regulatory reporting requirements

Employee Support & Vendor Coordination

• Serve as the primary contact for employees regarding complex benefit issues
• Interpret benefits policies and provide guidance to employees
• Act as the main liaison with plan providers to ensure efficient administration
• Oversee benefits-related communications and wellness initiatives

Lifecycle Administration & Orientation

• Manage benefit transactions across the employee lifecycle (new hire, life events, open enrollment, termination)
• Support new employee orientation with benefits-related content development and delivery
• Ensure timely and accurate employee support processes are in place

Systems & Data Management

• Oversee the Oracle Benefits Module, ensuring accuracy across events, changes, upgrades, and integrations
• Collaborate with Payroll, HRIS, HR Operations, Talent Acquisition, HR Partners, Legal, and IT to ensure seamless benefit administration
• Prepare special reports by collecting, analyzing, and summarizing data and trends
• Support mid-year and year-end HR events including performance and compensation cycles

Financial & Documentation Oversight

• Manage benefits invoicing and self-billing processes; ensure accuracy and timely payment
• Develop training materials and process documentation for benefit transactions

Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or related field
• 8–10 years of progressive experience in benefits administration preferred
• Strong working knowledge of HIPAA, ERISA, ACA, and other compliance requirements
• Experience with Oracle HRMS and advanced Excel (PivotTables, V-Lookups); proficiency in Word and PowerPoint
• Excellent communication skills with the ability to explain policies and processes clearly
• Proven ability to manage multiple priorities in a fast-paced, deadline-driven environment
• High attention to detail, confidentiality, and sound judgment in resolving issues
• Ability to work independently and cross-functionally across departments

Physical Requirements

• Prolonged periods of sitting and working at a computer