Commissions Manager

Sitetracker•New York, NY

9d•Remote

About The Position

Join our high-performing Finance team as Commissions Manager, a pivotal role offering full ownership of the commissions function for a ~400 person, multi-division organization, with direct visibility to the CFO. This is a rare chance to not just administer a process, but to rebuild it — inheriting a commissions environment built on Excel and manual reconciliation, and driving its transformation into a modern and strategic function. You'll bring analytical rigor and AI-powered insight to a process that has relied successfully on spreadsheets and institutional memory, with your work visible at the executive level from day one.

Requirements

Commission Calculation & Administration (Salesforce, Excel, NetSuite, Commission Software Platforms, AI Tools)
Bring hands-on fluency in Excel at an advanced level — you build and audit complex calculation models before you replace them.
Work from the Bookings dataset as the commissionable source of truth — Salesforce-fed, but adjusted for post-close changes — and NetSuite for GL posting and expense reconciliation.
Fluency with modern data and AI tooling is a strong differentiator — SQL, Python, and agentic AI development tools such as Claude Code.
Bring a proven track record of personally leading a systems transformation — replacing manual, spreadsheet-based processes with software.
Evaluate and implement a commissions platform such as CaptivateIQ, Spiff, or Xactly, including data migration and change management.
Design the governance structure, controls, and documentation that go with a new platform.
Leverage AI tools (ChatGPT, Claude, Copilot, or similar) to accelerate variance analysis and improve the quality of explanations.
Serve as the primary point of contact for commission inquiries and disputes, with a documented resolution process.
Communicate complex commission calculations clearly — to a rep who believes they were underpaid, and to an executive who wants the one-number summary.
Coordinate seamlessly across Sales Operations, People/HR, Legal, and Accounting to ensure plan documents, quota letters, and accruals are accurate and timely.
Produce clear monthly summaries of commission expense drivers, attainment distributions, and anomalies for Finance leadership.
Build trust with a 300+ person commission-eligible organization by being consistent, transparent, and fast to resolve issues.
Develop a deep, working understanding of every current commission plan, calculation methodology, and Excel-based process.
Achieve a seamless, error-free transition of commission calculation ownership, ensuring no missed or late payout cycles.
Establish a documented dispute-resolution process and become the trusted point of contact for commission inquiries.
Develop a clear, CFO-approved roadmap for commissions platform migration, including vendor evaluation and selection.
Deliver an initial plan rationalization analysis, identifying redundancy and proposing a simplified structure for the next fiscal year.
Implement a recurring, AI-assisted variance analysis and reporting process for Finance leadership.
Successfully complete migration of commissions administration onto a modern platform (CaptivateIQ, Spiff, Xactly, or comparable).
Launch the rationalized commission plan structure for the new fiscal year in partnership with Sales leadership and HR.
Ensure zero material commission calculation errors and consistent, on-time payout cycles across all divisions.

Nice To Haves

AI Tools
SQL
Python
Agentic AI development tools such as Claude Code
CaptivateIQ
Spiff
Xactly
ChatGPT
Claude
Copilot

Responsibilities

Own monthly and quarterly commission calculations for ~250 commission-eligible employees across sales, customer success, and other variable-comp roles, working across a wide range of bespoke plan structures.
Lead the technology transformation of commissions — owning the roadmap and execution of migrating the function that currently lives entirely in Excel and into a purpose-built software platform or some hybrid alternative.
Partner with the leadership across multiple functions and the People Operations team to rationalize plan complexity for the next fiscal year.
Serve as the primary point of contact for commission disputes, bringing a documented, defensible resolution process.
Apply AI tools to accelerate actuals vs. projections analysis and assist in explanation of commission outcomes with speed and clarity.
Own monthly and quarterly commission calculations across 300+ commission-eligible employees and highly bespoke plan structures.
Demonstrate in-depth knowledge of commission calculation mechanics, including accelerators, tiered payouts, SPIFs, and clawback provisions.
Work from the Bookings dataset as the commissionable source of truth — Salesforce-fed, but adjusted for post-close changes — and NetSuite for GL posting and expense reconciliation.
Executive reporting on variances and attainment to plan on rolling basis.
Ensure timely, accurate, and clearly communicated commission payouts to payees every cycle.
Lead a structured effort to analyze existing plan complexity, identify redundancy, and simplify the plan architecture.
Partner with BU leadership and HR to design a simpler, more scalable commission plan structure for the next fiscal year.
Critically evaluate why plans are structured the way they are, not just how to calculate them.
Bring a proven track record of simplifying a complex commission plan landscape, not just administering what exists.
Document plan logic and assumptions so that plan design decisions are transparent and auditable over time.
Own the end-to-end roadmap for migrating commissions out of Excel and into a purpose-built commissions platform.
Bring a proven track record of personally leading a systems transformation — replacing manual, spreadsheet-based processes with software.
Evaluate and implement a commissions platform such as CaptivateIQ, Spiff, or Xactly, including data migration and change management.
Design the governance structure, controls, and documentation that go with a new platform.
Leverage AI tools (ChatGPT, Claude, Copilot, or similar) to accelerate variance analysis and improve the quality of explanations.
Serve as the primary point of contact for commission inquiries and disputes, with a documented resolution process.
Communicate complex commission calculations clearly — to a rep who believes they were underpaid, and to an executive who wants the one-number summary.
Coordinate seamlessly across Sales Operations, People/HR, Legal, and Accounting to ensure plan documents, quota letters, and accruals are accurate and timely.
Produce clear monthly summaries of commission expense drivers, attainment distributions, and anomalies for Finance leadership.
Build trust with a 300+ person commission-eligible organization by being consistent, transparent, and fast to resolve issues.
Develop a deep, working understanding of every current commission plan, calculation methodology, and Excel-based process.
Achieve a seamless, error-free transition of commission calculation ownership, ensuring no missed or late payout cycles.
Establish a documented dispute-resolution process and become the trusted point of contact for commission inquiries.
Develop a clear, CFO-approved roadmap for commissions platform migration, including vendor evaluation and selection.
Deliver an initial plan rationalization analysis, identifying redundancy and proposing a simplified structure for the next fiscal year.
Implement a recurring, AI-assisted variance analysis and reporting process for Finance leadership.
Successfully complete migration of commissions administration onto a modern platform (CaptivateIQ, Spiff, Xactly, or comparable).
Launch the rationalized commission plan structure for the new fiscal year in partnership with Sales leadership and HR.
Ensure zero material commission calculation errors and consistent, on-time payout cycles across all divisions.