Principal Strategy Analyst
CarGurus LLC, Boston, MA, United States
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 Strategic Initiatives: Lead high-impact, enterprise-level problem solving
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
Thought Partnership & Internal Consulting
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
Competitive & Business Intelligence
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
Company Strategy
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
Team Development & Analytical Leadership
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
What You’ll Bring
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
Preferred Qualifications
Experience in marketplaces, technology, automotive, or related industries
Exposure to M&A, partnerships, or corporate development
MBA or equivalent advanced degree
The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles. Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training. This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs).
Position Pay Range $124,000 — $155,000 USD
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
#J-18808-Ljbffr
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 Strategic Initiatives: Lead high-impact, enterprise-level problem solving
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
Thought Partnership & Internal Consulting
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
Competitive & Business Intelligence
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
Company Strategy
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
Team Development & Analytical Leadership
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
What You’ll Bring
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
Preferred Qualifications
Experience in marketplaces, technology, automotive, or related industries
Exposure to M&A, partnerships, or corporate development
MBA or equivalent advanced degree
The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles. Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training. This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs).
Position Pay Range $124,000 — $155,000 USD
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
#J-18808-Ljbffr