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.

What You'll Bring

• Bachelor's degree in Finance, Accounting, Business Administration, or a related field.
• At least 4-6 years of relevant experience in financial analysis, sales compensation, sales operations, or a related function, with increasing ownership of complex analysis and business recommendations.
• Advanced financial modeling and analytical skills, including experience building scenario models, validating assumptions, and evaluating financial and operational impacts.
• Advanced proficiency in Excel or Google Sheets, with the ability to build accurate, scalable, and clearly documented models.
• Excellent written communication and presentation skills, with the ability to turn complex or ambiguous information into concise narratives and actionable recommendations for executive audiences.
• 2 years of experience working directly with executive stakeholders, presenting findings, discussing tradeoffs, and influencing decisions preferred.
• Strong business acumen and structured problem-solving skills, including the judgment to challenge assumptions constructively and connect detailed analysis to broader business priorities.
• Demonstrated ability to lead cross-functional initiatives, build effective relationships, and drive alignment across organizational boundaries.
• Experience with sales compensation structures, quota setting, and commission processes.
• Experience with CaptivateIQ or a comparable commission platform and familiarity with Salesforce; hands-on configuration and troubleshooting experience is preferred.
• Strong attention to detail, ownership, and project management skills, with the ability to work independently and manage multiple priorities in a fast-paced environment.
• SQL and Python are a plus, not required.

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
$115,000 - $145,000 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.
CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate.
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