Principal Financial/Sales Commissions Analyst

CarGurus•Boston, MA

6d•$115,000 - $145,000•Hybrid

About The Position

CarGurus is seeking an experienced Principal Financial/Sales Commissions Analyst to translate financial and sales performance data into actionable insights that inform sales compensation strategy and business decisions. Reporting to the Director of Sales Incentives, this role partners with senior leaders across Sales, Finance, and Go-to-Market (GTM), leads financial modeling and evaluation of incentive plan effectiveness, and presents findings and recommendations to executive leadership. The position calls for strong business judgment, the ability to structure ambiguous problems, and confidence engaging senior stakeholders on complex decisions and tradeoffs. The analyst leads commission plan modeling and the quarterly quota-setting process, and helps strengthen the systems, processes, and controls that support accurate, predictable commission payments. The role also provides technical leadership for CaptivateIQ and supports business planning, forecasting, performance evaluation, audit readiness, and cross-functional projects. CarGurus describes its work environment as using a flexible hybrid model. The role may qualify for discretionary bonuses or incentives and Restricted Stock Units (RSUs), in addition to benefits. The listed annual pay range is $115,000–$145,000 USD.

Requirements

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 building scenario models, validating assumptions, and evaluating financial and operational impacts.
Advanced proficiency in Excel or Google Sheets and ability to build accurate, scalable, clearly documented models.
Excellent written communication and presentation skills, including the ability to turn complex or ambiguous information into concise narratives and actionable recommendations for executive audiences.
Strong business acumen and structured problem-solving skills, including 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.
Strong attention to detail, ownership, and project management skills, with ability to work independently and manage multiple priorities in a fast-paced environment.

Nice To Haves

Two years of experience working directly with executive stakeholders, presenting findings, discussing tradeoffs, and influencing decisions.
Experience with CaptivateIQ or a comparable commission platform and familiarity with Salesforce; hands-on configuration and troubleshooting experience is preferred.
SQL and Python.

Responsibilities

Lead financial analysis and modeling to evaluate incentive plan designs, quota scenarios, and GTM changes, including impacts on sales performance, compensation expense, and business objectives.
Develop executive presentations and recommendations that explain analysis, assumptions, findings, risks, and tradeoffs.
Partner with senior leaders across Sales, Finance, GTM, and other functions to assess business needs, evaluate alternatives, and build alignment on compensation and quota decisions.
Analyze attainment, payout trends, and plan effectiveness to identify performance drivers, risks, and opportunities to improve incentive design.
Lead the quarterly quota-setting process, coordinating inputs, validating assumptions, modeling allocations, and driving timely execution.
Develop and maintain scalable financial models and reporting for business planning, forecasting, and performance evaluation.
Provide technical leadership for CaptivateIQ, including plan configuration, data integration, troubleshooting, and optimization 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, manage competing priorities, and communicate progress, findings, and decisions to stakeholders.

Benefits

Equity for all employees, both when they start and as they continue to grow.
Career development programs.
Corporate giving programs.
Employee resource groups (ERGs) and communities.
Flexible hybrid model.
Robust time-off policies.
Daily free lunch.
New car discount.
Meditation and fitness apps.
Commuting cost coverage.
The role may qualify for discretionary bonuses or incentives and Restricted Stock Units (RSUs).