Principal Strategy Analyst

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 The Corporate Strategy team is seeking a highly analytical, intellectually rigorous, and self-directed Principal Strategy Analyst to help shape the future direction of CarGurus. This individual will operate as a senior individual contributor within Corporate Strategy, leading high-impact, enterprise-level strategic initiatives alongside Strategy team leadership and serving as a trusted thought partner to senior leadership. The Principal Strategy Analyst will work across functions to define complex business problems, develop structured recommendations, and translate strategic insights into actionable plans that drive measurable outcomes. This person is expected to be an operator and a strategist; someone that understands the implications of the work they drive at all levels. In addition to leading critical initiatives, this role serves as an internal strategy consultant - partnering with business leaders across the company to clarify priorities, evaluate trade-offs, and elevate the quality of strategic decision-making. This position reports into the Corporate Strategy function and works closely with executive leadership and cross-functional partners across the organization What you'll do Scope and lead complex strategic initiatives aligned to company-wide priorities with input from strategy team leadership Structure ambiguous business questions into clear hypotheses, analytical frameworks, and execution plans Develop rigorous business cases, financial models, and scenario analyses to inform investment and resource allocation decisions Synthesize insights into executive-ready materials that clearly articulate recommendations, risks, and trade-offs Drive initiatives beyond recommendation — partnering with stakeholders to translate strategy into implementation roadmaps Serve as a trusted thought partner to leaders across the organization Act as an internal strategy consultant, supporting business units in evaluating growth opportunities, operational trade-offs, and strategic direction Lead structured problem-solving sessions with cross-functional teams to align on priorities and unlock progress Pressure-test assumptions, challenge conventional thinking, and improve decision quality through analytical rigor and intellectual honesty Provide strategic guidance that balances long-term positioning with near-term execution realities Develop a deep understanding of the automotive and marketplace landscape, including competitive dynamics and emerging trends Aggregate and synthesize insights from internal data, market research, and external sources Deliver clear, actionable insights that inform company strategy and market-level responses Support development of perspectives on new business opportunities, adjacencies, and potential investments Partner with senior leadership to support annual and multi-year strateg ... (truncated, view full listing at source)