Principal Strategy Analyst

CarGurus • Boston, MA

2d • Hybrid

About The Position

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

Requirements

• 5–7+ years of relevant professional experience, including strategy consulting, corporate strategy, investment analysis, or equivalent experience
• Remarkably high bias for action in all aspects of your work with a notably low ego
• Demonstrated ability to independently lead complex, ambiguous strategic initiatives from framing through recommendation and implementation
• Strong business judgment and structured problem-solving capabilities
• Advanced analytical skills and proficiency in Microsoft Excel and PowerPoint
• Exceptional written and verbal communication skills, with the ability to influence senior stakeholders
• Experience working closely with executive leadership and influencing without direct authority
• Ability to manage multiple high-priority initiatives in a fast-paced, evolving environment

Nice To Haves

• Experience in marketplaces, technology, automotive, or related industries
• Exposure to M&A, partnerships, or corporate development
• MBA or equivalent advanced degree

Responsibilities

• 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 strategic planning processes
• Evaluate strategic priorities and ensure alignment between corporate resources and long-term objectives
• Contribute to leadership off-sites and key decision forums with structured analysis and clear recommendations
• Support evaluation of inorganic growth opportunities and major investment decisions as needed
• Raise the analytical and problem-solving bar across the Corporate Strategy team
• Mentor junior team members on structured thinking, modeling, and executive communication
• Develop reusable frameworks and best practices that improve team efficiency and impact
• Contribute to a collaborative, high-performance culture grounded in rigor, accountability, and trust

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal