Associate People Operations Specialist

CarGurus is the largest and fastest-growing automotive marketplace, focused on bringing trust and transparency to car shopping. The Associate People Operations Specialist provides administrative and operational support across benefits, payroll, HR systems, and employee lifecycle processes, ensuring high-quality People Operations support and enhancing the employee experience.

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

Skills

• 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

Benefits

• Discretionary bonuses/incentives
• Restricted Stock Units (RSUs)
• Equity for all employees, both when they start and as they continue to grow with us
• Career development and corporate giving programs
• Employee resource groups (ERGs) and communities
• A flexible hybrid model
• Robust time off policies
• Daily free lunch
• A new car discount
• Meditation and fitness apps
• Commuting cost coverage

Company Overview