Associate People Operations Specialist

About Us

At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. We’re the largest and fastest-growing automotive marketplace, profitable for over 15 years.

The market is evolving, and we are too, moving the entire automotive journey online and guiding customers through every step—from selling an old car to financing, purchasing, and delivering a new one. Tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products.

We have a people-first culture that fosters kindness, collaboration, and innovation, empowering employees with tools to fuel career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives—come join us for the ride!

About the Role

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.

Responsibilities

• Benefits Administration & Vendor Management
  • Manage global benefits operations across the US, Canada, UK, and Ireland, overseeing benefit administration, invoice tracking, and processing/reconciliation of payments across ~20 vendors (medical, dental, 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.
• HR Systems & Data Management
  • 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.
• Employee Support & Communications
  • 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.
• Programs & Operational Support
  • 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.
• Payroll & Compliance
  • 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.

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/Ireland.
• Understanding of system integrations and troubleshooting.
• Working knowledge of benefits regulations across all locations (US/UK/Ireland), including COBRA, FSA/HSA administration, pension contributions, and associated tax implications (e.g., UK/Ireland 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.

Pay

The expected annual base salary range for this position is $57,000—$72,000 USD. Individual pay is determined by work location and factors such as job-related skills, experience, and relevant education or training. This role may also qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs).

Benefits

• Best-in-class benefits and compensation, including equity for all employees (both at hire and as they grow).
• Career development and corporate giving programs.
• Employee resource groups (ERGs) and communities for connection and impact.
• Flexible hybrid work model and robust time off policies for work-life balance.
• Daily free lunch, new car discount, meditation and fitness apps, and commuting cost coverage.