Principal Financial/Sales Commissions Analyst

CarGurus•Boston, MA
•Hybrid

About The Position

CarGurus is seeking an experienced Principal Financial/Sales Commissions Analyst to turn complex 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 incentive plan evaluation, and presents recommendations to executive leadership. The analyst will lead commission plan modeling and quarterly quota setting while strengthening the systems, processes, and controls that support accurate and predictable commission payments. The role requires strong business judgment, structured problem-solving, advanced analytical and financial modeling skills, and confidence engaging senior stakeholders on complex decisions and tradeoffs. It also provides technical leadership for CaptivateIQ, supports commission calculations and payout issue resolution, and leads process improvements, controls, special projects, and ad hoc analyses. CarGurus describes its work environment as flexible and hybrid and offers compensation and benefits, equity, career development programs, employee resource groups, time-off policies, and other perks. The stated 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, including the ability to build accurate, scalable, and 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 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.
  • Strong attention to detail, ownership, and project management skills, with the 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 experience.

Responsibilities

  • Lead financial analysis and modeling to evaluate incentive plan designs, quota scenarios, and go-to-market changes, including their effects on sales performance, compensation expense, and business objectives.
  • Translate complex analyses into clear executive presentations and recommendations that explain findings, assumptions, risks, and tradeoffs.
  • Partner with senior leaders across Sales, Finance, GTM, and other functions to assess business needs, evaluate alternatives, and align 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 by coordinating inputs, validating assumptions, modeling allocations, and driving timely execution.
  • Develop and maintain scalable financial models and reporting for 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 accurate, timely 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
  • Career development programs
  • Corporate giving programs
  • Employee resource groups and communities
  • Flexible hybrid model
  • Robust time-off policies
  • Daily free lunch
  • New car discount
  • Meditation and fitness apps
  • Commuting cost coverage
  • May qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs)
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