Associate People Operations Specialist

CarGurus•Boston, MA

7d•$57,000 - $72,000•Hybrid

About The Position

The Associate People Operations Specialist provides administrative and operational support across benefits, payroll, HR systems, and employee lifecycle processes. This role is critical to delivering accurate, compliant, and high-quality People Operations support while enhancing the overall employee experience. The role focuses on executing established workflows, maintaining employee and benefits data, managing vendor coordination, and responding to employee queries. The ideal candidate is detail-oriented, technically proficient, and capable of managing multiple priorities across global programs.

Requirements

1–2 years of experience in benefits administration or HR operations
Strong proficiency in Google Sheets (or Microsoft Excel) to organize and analyze data, with a solid grasp of Pivot Tables and functions like VLOOKUP.
Experience with HRIS systems, particularly Workday Benefits Administration module
Comfort working with data and systems
Strong data entry and reconciliation capabilities
Familiarity with benefits administration platforms across US / UK / IE
Understanding of system integrations and troubleshooting
Working knowledge of benefits regulations across all locations (US/ UK/ IE), including COBRA, FSA/HSA administration, pension contributions and associated tax implications (i.e UK/IE pension auto-enrolment and payroll deductions for medical/dental benefits)
Basic understanding of life insurance and Evidence of Insurability processes
Familiarity with payroll processing and vendor management

Responsibilities

Manage global benefits operations across the US, Canada, UK, and Ireland, overseeing benefit administration, invoice tracking, and the processing and reconciliation of payments across approximately 20 vendors (including medical, dental, and life insurance)
Conduct monthly audits of benefit plans, identifying discrepancies and driving resolution
Administer global pension and retirement schemes (UK, Ireland, US), including system uploads and quarterly fee tracking
Oversee FSA/HSA funding aligned with payroll cycles, including quarterly employer contributions
Administer COBRA processes and maintain associated tracking documentation
Manage Evidence of Insurability (EOI) approvals and send follow-ups for pending submissions
Maintain accurate employee data across Workday and related systems
Review and approve Qualified Life Event (QLE) benefit changes, including manual FSA/HSA adjustments
Process benefits onboarding, employee changes, beneficiary updates, and one-time employee payments (e.g., bonuses, reimbursements).
Monitor and troubleshoot weekly benefits integration files to ensure data accuracy and integrity
Run and review reports including Terminated with Benefits, Business Process Transactions, and quarterly dependent/beneficiary audits
Manage employee queries via ticketing systems (e.g., JIRA)
Provide support for benefits platforms and respond to FAQs
Coordinate employee communications, including onboarding reminders, benefits education, and wellness program updates
Maintain global Benefits Wiki and internal documentation, ensuring accuracy and accessibility
Administer commuter and parking programs, including enrollments, terminations, and funding file coordination
Plan and coordinate on-site and virtual events, including the annual Open Enrollment Fair
Support absence tracking, time-off administration, and other operational tasks that enhance employee experience and team efficiency
Manage employee payroll deductions for Ireland and UK benefits
Support unemployment claim documentation and responses
Ensure compliance with regulatory requirements across benefits, payroll, and related programs