Description:

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 CarGurus.com 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, pragmatic, and strategic Director of Legal to lead our litigation and labor & employment functions. This role will manage a diverse portfolio of legal matters, including employment issues, complex litigation, regulatory risk, and internal investigations. This role requires a clear communicator and strategic thinker who balances business opportunity with legal risk, exercises sound judgement, and earns trust through prepared, concise, and actionable advice.

The ideal candidate will be both a proactive legal strategist and a pragmatic business partner — capable of anticipating legal challenges, advising with conviction, and driving solutions that align with CarGurus' culture and growth objectives.

What You'll Do:
Litigation & Regulatory Risk Management

Lead and manage all litigation, pre-litigation, and dispute resolution matters, including commercial, consumer, employment, intellectual property, and regulatory actions.
Develop and execute litigation strategies that balance business priorities with risk mitigation and cost efficiency.
Oversee and coordinate responses to government inquiries, subpoenas, audits, and enforcement actions.
Manage relationships with outside counsel, ensuring pragmatic, high-quality, efficient, and cost-effective representation.
Monitor legal and regulatory developments and translate complex requirements into clear, actionable guidance for business leaders.

Labor & Employment

Serve as the primary and trusted legal advisor on employment matters, including hiring, compensation, employee relations, investigations, performance management, and terminations, providing practical, timely, and pragmatic counsel.
Advise on compliance with federal, state, and international employment laws, including wage and hour, discrimination, harassment, disability accommodation, and workplace safety.
Partner closely with People & Talent team to develop, maintain, and communicate employment policies and practices.
Oversee internal investigations and manage responses to agency claims and employment litigation.

What you'll bring

Juris Doctor (JD) from an accredited law school and active membership in at least one U.S. state bar, with the ability to qualify for admission as in-house counsel in Massachusetts.
10+ years of relevant legal experience, including significant in-house experience (preferably in the technology sector).
Proven expertise in litigation management, employment law, and regulatory risk.
Demonstrated ability to exercise sound judgement, instincts, and business pragmatism under pressure.
Exceptional clarity in oral and written communication and able to distill complex legal issues into concise, actionable recommendations.
Confidence and preparation in delivering advice and managing high stakes matters.
Ability to manage multiple priorities in a fast-paced, high-growth environment.
Demonstrated leadership ability, including experience hiring, mentoring, and developing junior attorneys, as well as managing outside counsel.
Exposure to technology-related regulatory issues such as intellectual property, data privacy, and advertising.
Collegial, team-oriented mindset.

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