Principal Financial/Sales Commissions 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 CarGurus Sales Commissions team is seeking an experienced Principal Financial / Sales Commissions Analyst with exceptional analytical, financial modeling, and communication skills. Reporting to the Director of Sales Incentives, this role will translate complex financial and sales performance data into actionable insights and recommendations that inform sales compensation strategy and business decisions. As a key partner to senior leaders across Sales, Finance, and Go-to-Market (GTM), you will lead financial modeling, evaluate incentive plan effectiveness, and present findings and recommendations to executive leadership. Success requires strong business judgment, the ability to structure ambiguous problems, and confidence engaging senior stakeholders on complex decisions and tradeoffs. You will also lead commission plan modeling and the quarterly quota-setting process, while helping strengthen the systems, processes, and controls that support accurate and predictable commission payments. What You’ll Do • Lead financial analysis and modeling to evaluate incentive plan designs, quota scenarios, and GTM changes, assessing their impact on sales performance, compensation expense, and business objectives. • Translate complex analysis into clear executive insights , developing presentations and recommendations that explain key findings, assumptions, risks, and tradeoffs. • Partner closely with senior leaders across Sales, Finance, GTM, and other functions to understand business needs, evaluate alternatives, and build alignment on compensation and quota decisions. • Analyze attainment, payout trends, and plan effectiveness to identify performance drivers, emerging risks, and opportunities to improve incentive design. • Lead the quarterly quota-setting process, coordinating inputs, validating assumptions, modeling allocations, and driving timely execution across stakeholders. • Develop and maintain scalable financial models and reporting that support business planning, forecasting, and ongoing performance evaluation. • Provide technical leadership for CaptivateIQ, including plan configuration, data integration, troubleshooting, and optimization in partnership with the commission team. • Partner with the commission team to validate calculations, investigate complex payout issues, and support timely, accurate commission payments. • Improve and document repeatable processes, strengthen SOX controls, and maintain audit-ready support for commission calculations and plan changes. • Lead special projects and ad hoc analyses, managing competing priorities and communicating progress, findings, and decisions to stakeholders.