Senior Director, Total Rewards



Sales & Business Development
Cambridge, MA, USA
Posted on Tuesday, May 21, 2024

Who we are

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. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years.

What we do

The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!

Role Overview:

CarGurus is seeking an experienced Senior Director of Total Rewards and People Operations who will develop a consistent rewards and operations framework that delivers an exceptional employee experience, in line with CarGurus' business needs, culture, and values. Operating with a financial and business-focused mindset, you will be a key advisor to business leadership to ensure careful management of resources while delivering distinctive Total Rewards. You will lead all aspects of CarGurus’ compensation, benefits, and rewards programs, as well as our People Operations team, including payroll and compliance activities. Reporting to the Chief People Officer, and as a People & Talent leadership team member, you will provide thought leadership and strategic perspective, shaping the People agenda at CarGurus.

What you’ll do

People Strategy & Leadership:

  • As a senior People & Talent leadership team member, you will help shape the People agenda at CarGurus.
  • Together with business leaders, you will help build a culture that is open and connected and strives for the highest standard of behavior and ethical conduct.
  • You will partner with and advise the business about all people-related policies, programs, and initiatives while driving continuous improvement across Total Rewards & People Operations.
  • You will participate in the development and execution of critical initiatives tied to our corporate strategy and in support of clear business goals.
  • Apply the lens of diversity, inclusion, and equity to all compensation, benefits, and long-term incentive programs, ensuring that plan design and administration are conducted in a manner that treats all team members equitably, regardless of background.
  • Remain current on compensation and benefits standard methodologies and the changing legal landscape and assess and communicate the potential impact on the business, along with providing recommendations/solutions to address concerns.
  • Architect processes and technology in an employee-centric manner, always focused on the employee experience, with the intent of embracing and enhancing the CarGurus culture.
  • Develop communication strategies for total rewards programs that will creatively and effectively attract and retain key talent, enabling the organization to meet key priorities and the needs of the business.


  • Lead the design, strategy, planning, management, and communications of compensation, benefits, and incentive pay philosophy and programs (bonus, equity, and long-term incentives) for CarGurus, ensuring alignment with the long-term strategy and desired culture of our business.
  • Oversee Executive Compensation plan design and execution, inclusive of preparation of board materials and interaction with board members as needed.
  • Oversee equity plan administration, maintain accurate records of vesting schedules, and execute settlements in compliance with plan rules and payroll tax requirements.
  • Lead the annual merit planning process and communications, and ensure our technology is optimized to support an easy and smooth process for the business.
  • Demonstrate your leadership by providing expert counsel to HR and Business leadership on compensation issues related to company pay structures, pay change recommendations, new hire offers, and wage and hour regulations.
  • Conduct market research/analysis to determine if changes are necessary to current pay practices to remain competitive and to ensure internal and external equity.
  • Oversee the payroll function and ensure accuracy in all pay practices.

Benefits and Perks

  • Lead a comprehensive assessment of current benefit plans and develop data-driven recommendations for strategy, plan design, and cost structure changes to ensure that we maintain competitive advantage and meet the needs of our team members and company strategy and culture, positioning CarGurus as a top place to work within the geographies in which we operate.
  • Maintain compliance by overseeing the administration of all team member benefit programs (including worker’s compensation, insurance, leave of absence, etc.).
  • As a subject matter expert, build awareness and education programs for employees at all levels in all areas of Total Rewards to ensure an understanding of their collective value.
  • Establish and execute wellness strategies to improve our team members’ experience and coordinate planned initiatives and programs.
  • Execute all people & talent processes efficiently, as seamlessly as possible to the employee.
  • Act as subject matter expert for CarGurus’ policies in alignment with our values, appropriate laws, and regulations; assess existing and create new policies, and ensure global consistency and cross-functional collaboration with Legal and other teams.
  • Be a partner with our Legal advisors, IT, and Finance teams to support compliance and protect CarGurus.
  • Ensure plan compliance with regulatory filings and updates, notices, ACA mandates & reporting, plan audits, and non-discrimination testing.
  • Prepare audit documentation to ensure SOX compliance.
  • With an eye for important regulations, ensure all CarGurus-related administrative forms, reports, processes, and audits are completed accurately, timely, and in compliance with relevant local, state, federal, and provincial regulations for Benefits, HR Recordkeeping, and audits and compliance.

Who you are

  • You’re a Catalyst for Impact with a strong performance orientation, demonstrating ownership for your work and a passion to achieve key outcomes, strong analytical and problem-solving skills, and an ability to roll up your sleeves and get stuff done.
  • You’re a Coach who brings strong conscientious people management capability with success in building and leading high-performing teams.
  • You’re a strong Communicator, sharing our vision and bringing people along.
  • You’re a Change Leader with a proven track record of applying fresh, creative ideas to long-standing complex challenges.
  • You’re a Caring Collaborator, able to build relationships and influence business leaders at all levels including the executive team.
  • You’re purpose and values-driven, with a reputation for integrity, ownership, and inclusion.

What you’ll bring

  • 10-15 years of Total Rewards and People Operations experience, including being responsible for the entire compensation & benefits function, including design, administration, and compliance.
  • Experience working with compensation plan design, job frameworks, pay structures, job evaluation processes, and benchmark salary data.
  • Experience coordinating equity programs required (restricted stock units and stock options).
  • Experience with short and long-term incentive plan design, administration, and other ways to incentivize people to live the culture, deliver on strategic objectives, and drive sustainable long-term growth.
  • Experience with international and domestic payroll and benefits administration.
  • Experience designing and drafting policies and operational procedures that deliver an outstanding employee experience, including working with the Legal team and influencing senior leadership to obtain final approval.
  • Knowledge & understanding of HR (local/state/federal) laws.
  • Strong project management, organizational, and analytical skills to support data analysis and reporting.
  • Very strong communication and influencing skills with the ability to effectively convey messages to different leaders and ensure team members understand total rewards, policies, and their accountabilities.
  • A track record of managing, leading, and developing a team.
  • Demonstrated success in fast-growing organizations with best-in-class processes and in entrepreneurial environments where you’ve had to roll up your sleeves to get things done.

Working at CarGurus

We reward our Gurus’ curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives.

We welcome all

CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential—starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That’s why we hope you’ll apply even if you don’t check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid