Manager, Sales Commissions - Contractor

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. Five9 is seeking a Manager, Sales Commissions to lead the end‑to‑end administration, governance, and evolution of its global sales commission programs. This role is responsible for ensuring accurate, timely, and compliant commission payments for sales and customer success representatives. The Manager will be responsible for overseeing the maintenance of an Incentive Compensation Management (ICM) tool, as well as ETL integrations and SOX controls related to commissions. This role combines hands‑on technical expertise, people leadership, and strong cross‑functional partnership across Finance, Sales Operations, Payroll, and Audit. Key Responsibilities Sales Commission Operations & Leadership Lead the end‑to‑end commission process for hundreds of quota‑carrying reps, ensuring accurate and timely payouts. Manage a small team, providing coaching, workload prioritization, and performance guidance. Act as the primary escalation point for commission disputes, complex calculations, and off‑cycle adjustments. Partner closely with Sales Operations, Deal Desk, Payroll, and HR to ensure alignment on compensation plans, bookings, and employee data. ICM Ownership & Commission Model Management Serve as the system owner for the Company ICM, including plan configuration, calculation logic, hierarchies, crediting rules, and rate tables. Design, maintain, and enhance commission models to support evolving compensation plans, new sales roles, SPIFFs, and business initiatives. Perform and oversee calculation validation, tie‑outs, and variance analysis prior to payout approval. Ensure scalability and auditability of models as the sales organization grows and plan complexity increases. Qualifications & Experience Required Qualifications 7+ years of experience in sales commissions, revenue operations, or compensation accounting, including people leadership experience. Deep hands‑on experience administering ICM tools Strong working knowledge of CRM and bookings systems. Experience supporting SOX‑controlled commission processes in a public company environment. Advanced Excel skills and strong financial reconciliation capabilities. Proven ability to work cross‑functionally with Finance, Sales Ops, Payroll, HR, and Audit. Key Competencies High attention to detail and data integrity Strong ownership mindset over mission‑critical financial processes Ability to balance operational execution with system and control improvements Clear communicator with the ability to explain complex commission logic to non‑technical stakeholders Trusted partner to Sales leadership and Finance executives Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer. Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.