: Sr. Director of Total Rewards and People Operations

Car shopping is complicated. At CarGurus, we use data and technology to make it simple, giving people the tools they need to confidently find, buy, finance, or sell a car. The best part? Our works made a real impact. Were the most-visited car-shopping site in the US, and were expanding globally. Ready to come along for the ride?

CarGurus seeks an experienced Senior Director of Total Rewards and People Operations who will develop a consistent rewards and operations framework in line with CarGurus business needs, culture, and values, including relevant programs addressing domestic and international benefits and compensation, compliance, and processes! You will lead all aspects of CarGurus compensation, benefits, and rewards programs, as well as lead our People Operations team including payroll and compliance. This Role will report to our Chief People Officer.

What You'll Do:

People Strategy & Leadership

  • As a senior member of the People & Talent leadership team, you will help shape the People agenda at CarGurus
  • Together with business leaders build a culture which is open and connected and strives for the highest standard of behavior and ethical conduct
  • Partner and advise the business around all people related policies, programs and initiatives
  • Participate in the development and execution of critical initiatives tied to our corporate strategy and in support of clear business goals

Compensation & Benefits

  • Lead the design, strategy, planning, management and communications of the compensation, benefits and incentive pay programs (bonus, equity and long-term incentives) for CarGurus
  • 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
  • Lead a comprehensive assessment of current benefit plans and develop data-driven recommendations for strategy, design and cost structure changes to ensure that we maintain a competitive advantage and meet the needs of our team members and the company
  • Demonstrate your leadership through 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 equity
  • Maintain compliance by overseeing the administration of all team member benefit programs (including workers compensation, insurance, leave of absence, etc.).
  • Develop communication strategies for total rewards programs which will creatively and effectively attract and retain key talent, enabling the organization to meet key priorities and the needs of the business.
  • As a SME, build awareness and education programs for employees at all levels in all areas of Total Rewards to ensure an understanding of their collective value.
  • Remain current on comp and benefits standard methodologies, changing legal landscape, assess and communicate potential impact on the business along with recommendations/solutions to address concerns
  • Establish and execute wellness strategy to improve our team members experience and coordinate planned initiatives and programs

People Operations

  • Lead the maintenance of CarGurus policies in alignment with our values, appropriate laws and regulations
  • Be a partner with our Legal advisors, IT, and Finance teams to support compliance and protect CarGurus
  • Oversee the People Operations team including functions of payroll and compliance
  • 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, you 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 Record-keeping and audits and compliance

Who You Are:

  • 10+ 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 structures, job evaluation process and benchmark salary data
  • Experience coordinating equity programs required (restricted stock units and stock options)
  • Experience with market-based pricing, short and long term incentive administration and other compensation frameworks
  • Experience with international and domestic payroll and benefits administration
  • Workday experience preferred
  • Experienced 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 outstanding processes AND entrepreneurial environments where youve had to roll up your sleeves and get things done

CarGurus Culture:

At CarGurus, we invest in our peoples professional growth with everything from learning and development programs to tuition reimbursement. Want to work on projects that expand your skill set without sacrificing your work/life balance? You got it. We also strive to provide perks and benefits that employees actually care about like free lunch, commuter subsidies, and more. That includes equity in the companyour way of showing that we want you here for the long haul.

We work hard every day to build the worlds most trusted and transparent automotive marketplace, but trust and transparency dont just apply to our consumers. They extend to our talent, too. We aim to create a workplace where everyone feels they can bring the ultimate expression of themselves and their potentialwhere you dont just fit, you thrive. We dont discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation.

In addition to the US, CarGurus operates sites in Canada and the UKwith other markets on the horizon. We have offices in Cambridge, MA; Detroit, MI; Dublin, Ireland; San Francisco, CA and London, UK. Check out our careers page to learn more.


Employee Testimonials


"At CarGurus, it’s important that our work around Diversity, Equity, and Inclusion truly creates belonging. Our goal is to ensure that everyone feels that they belong, that they can thrive and that their background, race, gender and intersectional identities are represented at all leadership levels across the company. We’re also striving to create more equity in our practices, and policies, and to foster a culture where inclusiveness is a reflex. This work is a journey, but we’re persistent and we look forward to growing and learning together along the way."


"We believe that learning happens every day and everywhere. It’s the success and foundation of our pioneering mindset, and each Guru plays a role in the fostering of our culture of learning. We challenge and support each other in staying curious, finding opportunities for growth, and learning through moments of discomfort so that we can become and show up as the best versions of ourselves."


"At CarGurus we're committed to empowering the professional growth of employees from all backgrounds by supporting them with the tools and opportunities to grow their careers at our company and beyond. This is ongoing work that encompasses all staff members, to support positive change within our organization and the industry as a whole."


"The PistonHeads team is small, which makes it easy for us to engage with new things. Our teams aren’t just good at collaborating, they’re naturally integrated, so new and experienced employees alike can quickly find themselves learning about parts of the business they haven’t worked in before. This is especially possible in editorial, where our work is intertwined with what other teams are doing."


"CarGurus has enabled and empowered me to invest in my growth. The people and passion here have inspired me to take on new challenges and not just develop my sales skills, but also explore leadership."


"As an engineer, one of the things that I love most about working at CarGurus is the opportunity to innovate while solving complex problems. I feel empowered with the trust my manager and team show in me. I have the creative freedom to pursue projects that might be outside of our traditional scope. At CarGurus, we believe in experimenting and learning from our failures. The receptivity to new ideas makes me feel inspired and valued, something I haven’t experienced at other tech giants I’ve worked with."