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Prove AIProve AINew York, NY

Director, Sales Compensation

Lead the design, implementation, and administration of complex sales commission plans for 100+ employees across Sales, CS, and Sales Engineering in a consumption-based model. Manage a team of two, drive AI-powered automation, deliver analytics/reporting to leadership, and ensure meticulous monthly accuracy while partnering with RevOps, Sales, and Finance.

190k – 215k/yr
Remote10+ YOERevenue Operations

About the role

Key Responsibilities

Strategic Planning & GTM Alignment:

  • Design, implement, and administer comprehensive sales commission plans for over 100 employees across Sales, Customer Success, Sales Engineering and other departments.
  • Partner closely with the SVP of Revenue Operations, Sales Leaders, and Finance to model, forecast, and align compensation strategies with overarching GTM objectives.
  • Assess the operational feasibility of proposed plans, ensuring that what is designed strategically can be accurately administered at scale.

Team Leadership:

  • Directly manage, develop, and mentor a high-performing team of two compensation professionals, overseeing their daily workflows, monthly deliverables, and professional growth.

Process Automation & AI Innovation:

  • Leverage compensation tools and technology to streamline processes, automate commission calculations, and improve overall operational efficiency.
  • Actively identify opportunities to utilize Artificial Intelligence (AI) to automate manual workflows, reconcile complex datasets, and accelerate the validation of commission outputs.

Standardized Reporting & Analytics:

  • Design, build, and standardize rigorous monthly and quarterly reporting packages tailored for Finance and Sales Leadership to track commission spend, budget variances, and plan effectiveness.
  • Gather and analyze sales data, performance metrics, and revenue trends to deliver data-driven insights and actionable recommendations for future plan modifications.

Meticulous Administration & Audit:

  • Oversee the monthly commission cycle with an elite standard of accuracy, including a commitment to personally review every single employee's statement in detail each month.
  • Master our primary commission tool (CaptivateIQ), while maintaining the architectural readiness and willingness to transition the entire process at a moment's notice.
  • Ensure all plans remain competitive, equitable, and compliant with relevant financial standards and regulations.

Cross-Functional Collaboration & Communication:

  • Act as a trusted advisor to sellers and sales leadership, creating clear, concise documentation and conducting regular feedback loops (surveys, town halls) to maintain high motivation and transparency.
  • Partner with Finance to establish bulletproof auditing, reconciliation, and expense forecasting workflows.

Qualifications

Experience:

  • 10+ years of dedicated experience in sales compensation design and administration, with a proven track record navigating the complexities of a consumption-based business model.
  • 3+ years of experience directly managing, mentoring, and evaluating direct reports within a revenue operations or corporate compensation environment.

Strategic & Operational Hybrid Mindset:

  • Proven ability to advise senior leadership on GTM strategy, paired with an explicit passion for commissions administration and getting the fine details right.

Tools & Technical Agility:

  • Advanced proficiency with commission automation platforms (specifically CaptivateIQ, though experience with Varicent or Xactly is welcome).
  • Practical exposure to utilizing AI tools or advanced automation scripts to streamline manual data reconciliation (Claude, Gemini).
  • Expert-level Google Sheets / Excel capabilities are mandatory.
  • Familiarity with the broader tech stack: Salesforce, Adaptive, Intacct.

Education & Certifications:

  • Bachelor's degree in Finance, Business Administration, or a related field; MBA or Certified Compensation Professional (CCP) designation preferred.

Core Skills:

  • Exceptional analytical problem-solving skills, rigorous attention to detail, and top-tier communication skills required to manage cross-functional stakeholders smoothly.

Compensation

The anticipated salary pay range for Metro 2 areas for this role is $200,000-$215,000 plus sales incentive plan. The anticipated salary pay range for Metro 3 areas for this role is $190,000-$210,000 plus sales incentive plan. Offered salary will be determined by the applicant's experience, knowledge, skills, geo-location and abilities as well as internal equity and alignment with market data.

Benefits & Perks for FTE Provers:

  • Competitive salaries & Bonus Plan (for eligible roles) and Equity Plan
  • Modern Health for financial, mental, and physical wellness
  • 401(k) Retirement Plan & Match (US Offices)
  • Unlimited Vacation and Flexible hours
  • Comprehensive medical benefits for you and your family
  • Emotional & Physical Wellness – Access to wellness services (EAP & Prove Well-Being Reimbursement)
  • Bottomless snacks & beverages for certain office locations
  • Daily GrubHub stipend for lunch if coming into the office (US Offices)

Skills

Sales Compensation DesignCommission AdministrationCaptivateiqVaricentXactlySalesforceGoogle SheetsExcelAI AutomationGo-to-Market StrategyRevenue OperationsFinancial Analysis
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