Director, Benefits
Headquartered in Boston, Massachusetts, CarGurus is the all-in-one platform that’s moving the entire car shopping journey online and guiding customers through each step. This includes everything from selling an old car to financing, purchasing, and delivering a new one. Today, millions of consumers visit cargurus.com each month, and more than 30,000 dealerships use our products. We have a people-first culture that fosters kindness, collaboration, and innovation, while empowering our Gurus with tools and resources to fuel their career growth. Our goal is to give all people—consumers, dealers, and our employees—the power to reach their destination.
Job Description
Role overview
We are seeking a strategic, people-first leader to serve as Director of Benefits and oversee the full scope of CarGurus’ global benefits programs. In this role, you will define and deliver a competitive, cost-effective benefits strategy that supports the diverse needs of our employees and aligns with our values and long-term business objectives.
As the most senior leader overseeing benefits, you will be responsible for designing, implementing, and continuously improving programs that span health and welfare, retirement, leave, wellbeing, and perks across the U.S., Canada, the UK, and Ireland. You’ll serve as a trusted advisor to senior leadership and a key partner to Finance, Legal, and HR stakeholders, ensuring that our offerings are compliant, market-relevant, and operationally sound.
This role blends strategic planning with hands-on leadership of program execution and team development—balancing big-picture thinking with the operational rigor required to deliver a high-impact employee experience.
What you'll do
Strategic Leadership & Program Design
- Own and evolve CarGurus’ global benefits strategy, ensuring offerings are competitive, inclusive, and aligned with employee needs and business priorities
- Analyze market trends, employee feedback, and internal data to drive thoughtful, data-informed enhancements to program design
- Collaborate with Finance to manage budgeting, cost modeling, and forecasting for all benefits-related programs and initiatives
Plan Management & Optimization
- Lead the design, implementation, and administration of employee benefits programs, including medical, dental, vision, life and disability insurance, 401(k), commuter benefits, tuition reimbursement, wellness programs, and other perks
- Continuously evaluate plan performance and utilization, identify opportunities for optimization, and ensure benefit offerings remain high-value and cost-effective
- Drive the annual Open Enrollment process, including communications, vendor coordination, and operational execution in partnership with HRIS and internal comms
Compliance & Vendor Oversight
- Ensure full compliance with all federal, state, and local regulations (ACA, ERISA, HIPAA, COBRA, etc.), as well as international benefits requirements where applicable
- Oversee all regulatory filings and reporting (e.g., 5500s, non-discrimination testing, Medicare Part D disclosures, CMS/HIRD reporting, etc.)
- Manage external broker and vendor relationships, negotiate renewals and contracts, and hold partners accountable to service-level standards
Leave, Accommodation & Employee Experience
- Oversee administration of leave of absence and accommodation programs including FMLA, ADA, parental leave, and disability
- Partner with Legal and People Business Partners to support escalated leave cases and ensure consistent, employee-centered handling
- Serve as the senior subject matter expert for benefits-related matters, providing guidance to the HR team and supporting employee escalations when needed
Cross-Functional Collaboration & Leadership
- Collaborate with HRIS, Payroll, Finance, Legal, and People Operations teams to ensure operational excellence and data integrity
- Develop and execute effective employee communication strategies to drive engagement and understanding of benefits offerings
- Lead and mentor a high-performing team, fostering a collaborative, growth-oriented culture within the benefits function
What you'll bring
- 15+ years of progressive experience in employee benefits, with ownership of program strategy, operations, and compliance
- Proven success overseeing domestic and international benefits programs, with deep understanding of industry trends and regulatory frameworks
- Demonstrated experience managing large-scale benefits budgets, vendor relationships, and cross-functional partnerships
- Strong analytical mindset with the ability to use data to drive decision-making and present insights to leadership
- Excellent written and verbal communication skills; ability to simplify complex topics for a broad audience
- High degree of integrity, discretion, and empathy in managing sensitive information and employee needs
- Familiarity with Workday or similar HRIS systems; CEBS certification or related credentials a plus
Role overview
We are seeking a strategic, people-first leader to serve as Director of Benefits and oversee the full scope of CarGurus’ global benefits programs. In this role, you will define and deliver a competitive, cost-effective benefits strategy that supports the diverse needs of our employees and aligns with our values and long-term business objectives.
As the most senior leader overseeing benefits, you will be responsible for designing, implementing, and continuously improving programs that span health and welfare, retirement, leave, wellbeing, and perks across the U.S., Canada, the UK, and Ireland. You’ll serve as a trusted advisor to senior leadership and a key partner to Finance, Legal, and HR stakeholders, ensuring that our offerings are compliant, market-relevant, and operationally sound.
This role blends strategic planning with hands-on leadership of program execution and team development—balancing big-picture thinking with the operational rigor required to deliver a high-impact employee experience.
What you'll do
Strategic Leadership & Program Design
- Own and evolve CarGurus’ global benefits strategy, ensuring offerings are competitive, inclusive, and aligned with employee needs and business priorities
- Analyze market trends, employee feedback, and internal data to drive thoughtful, data-informed enhancements to program design
- Collaborate with Finance to manage budgeting, cost modeling, and forecasting for all benefits-related programs and initiatives
Plan Management & Optimization
- Lead the design, implementation, and administration of employee benefits programs, including medical, dental, vision, life and disability insurance, 401(k), commuter benefits, tuition reimbursement, wellness programs, and other perks
- Continuously evaluate plan performance and utilization, identify opportunities for optimization, and ensure benefit offerings remain high-value and cost-effective
- Drive the annual Open Enrollment process, including communications, vendor coordination, and operational execution in partnership with HRIS and internal comms
Compliance & Vendor Oversight
- Ensure full compliance with all federal, state, and local regulations (ACA, ERISA, HIPAA, COBRA, etc.), as well as international benefits requirements where applicable
- Oversee all regulatory filings and reporting (e.g., 5500s, non-discrimination testing, Medicare Part D disclosures, CMS/HIRD reporting, etc.)
- Manage external broker and vendor relationships, negotiate renewals and contracts, and hold partners accountable to service-level standards
Leave, Accommodation & Employee Experience
- Oversee administration of leave of absence and accommodation programs including FMLA, ADA, parental leave, and disability
- Partner with Legal and People Business Partners to support escalated leave cases and ensure consistent, employee-centered handling
- Serve as the senior subject matter expert for benefits-related matters, providing guidance to the HR team and supporting employee escalations when needed
Cross-Functional Collaboration & Leadership
- Collaborate with HRIS, Payroll, Finance, Legal, and People Operations teams to ensure operational excellence and data integrity
- Develop and execute effective employee communication strategies to drive engagement and understanding of benefits offerings
- Lead and mentor a high-performing team, fostering a collaborative, growth-oriented culture within the benefits function
What you'll bring
- 15+ years of progressive experience in employee benefits, with ownership of program strategy, operations, and compliance
- Proven success overseeing domestic and international benefits programs, with deep understanding of industry trends and regulatory frameworks
- Demonstrated experience managing large-scale benefits budgets, vendor relationships, and cross-functional partnerships
- Strong analytical mindset with the ability to use data to drive decision-making and present insights to leadership
- Excellent written and verbal communication skills; ability to simplify complex topics for a broad audience
- High degree of integrity, discretion, and empathy in managing sensitive information and employee needs
- Familiarity with Workday or similar HRIS systems; CEBS certification or related credentials a plus
