Director, Sales Compensation

We are seeking an executive-facing, player-coach Director, Sales Commissions to lead the global strategy, plan design, execution, and analytics for our sales incentive compensation programs. Reporting to the VP of Finance Operations, you will serve as the subject matter expert and strategic partner to HR and Revenue leadership.This role bridges executive-level strategy with hands-on operational execution. You will design variable comp plans that align with company growth objectives, evaluate plan efficacy through deep performance analytics, and manage end-to-end execution through our commissions system, Everstage. You will oversee a distributed team of two individual contributors (located in the US and London), driving high performance, continuous process improvement, operational efficiency, and strict payout accuracy while leveraging modern tools like AI to transform day-to-day workflows.Reporting StructureThis role reports directly to the VP of Finance Operations

What You'll Be Doing:

• Lead the annual sales compensation plan design process across both B2B SaaS (recurring revenue) and non-recurring revenue business models. Translate company targets into effective incentive structures and comprehensive plan documentation.
• Executive Alignment: Model compensation scenarios, present strategic plan recommendations directly to the CRO and CFO, and lead iterative revisions to land final executive approval.
• Define and maintain clear governance policies for variable compensation, including leaves of absence (LOA), guarantees, ramps, plan exclusions, exception management, and mid-year quota adjustments.
• Partner closely with HR, Revenue, and Sales Operations to gather business inputs, align on role-based metrics, ingest quotas and territories, and ensure smooth plan rollout and policy enforcement.
• Oversee the end-to-end execution and calculation of all variable comp plans within Everstage. Drive flawless payout accuracy, timely execution, and clear communication to maintain organizational trust with payees.
• Review, validate, and sign off on monthly and quarterly global commission and bonus payroll workbooks across US and international schedules prior to submission to Payroll.
• Audit and optimize operational workflows within Everstage. Partner closely with HR Operations/HRIS on data pipeline syncs (Workday to Everstage) to monitor, audit, and resolve data quality gaps (e.g., transfers, promotions, new hires).
• Maintain a solid understanding of upstream deal structure and configuration within Salesforce CPQ. Resolve complex commissioning questions tied to stair-step deals, multi-year acceleration, early renewals, and custom contract terms.
• Serve as the primary decision-maker for first-level plan exceptions, dispute resolutions, and policy interpretations, formulating firm, data-backed recommendations prior to escalation.
• Executive & Board-Level Reporting: Build and deliver performance monitoring analytics, quota/plan attainment KPIs, and commission expense insights. Deliver board-pack inputs and present quarterly performance analytics to the CFO as part of Finance Operations Quarterly Business Reviews (QBRs).
• Partner with the Enterprise Data team to define business requirements, ensure data accuracy, and maintain reporting models within the company’s data warehouse (Snowflake) and reporting platforms (Tableau).
• Partner with FP&A and Accounting to provide accurate, data-driven inputs for commission expense forecasts, month-end/quarter-end commission accruals, and capitalized commissions.
• Lead, coach, and mentor a remote team of two analysts (US and London). Set clear performance expectations, foster individual professional growth, and drive a culture of accountability and support.
• Drive continuous innovation by actively experimenting with AI tools (e.g., Gemini, Claude) to streamline analytics, automate operational workflows, and empower the broader team to adopt modern technology

What You'll Bring:

• 8+ years of progressive experience in sales compensation or incentive management, including 5+ years of direct people management experience.
• Deep expertise designing and administering incentive plans in B2B SaaS / recurring revenue environments, along with experience accounting for non-recurring revenue models.
• Direct experience with commission management platforms (Everstage preferred, or equivalent SPM systems like CaptivateIQ, Spiff, Xactly). Advanced Excel skills for financial modeling.
• Experience partnering with HRIS systems and data pipelines (Workday to Everstage integration experience strongly preferred).
• Familiarity partnering with data teams on requirements for data warehousing and analytics platforms (Tableau and Snowflake experience is a plus).
• Operational understanding of Salesforce CPQ, deal flows, quote-to-cash processes, and complex contract mechanics (e.g., stair-steps, multi-year).
• Player-Coach Mindset: Willingness to roll up your sleeves to perform detailed analytics and operational execution while guiding strategic direction.
• Superior verbal and written communication skills with a proven ability to present complex financial models, defend plan designs, and present quarterly business results to executive leadership (CFO, CRO, VPs).
• Strong business acumen to independently evaluate exception requests and provide firm, well-reasoned recommendations.
• Strong coaching and performance management capabilities suited for a distributed, remote team environment.
• An innovative mindset with a desire to experiment with and drive team adoption of emerging technologies and AI platforms (e.g., Claude).