Manager, Sales Commissions

Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. We celebrate diversity and foster an inclusive environment, empowering employees to be their authentic selves.

About the role

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 ensures accurate, timely, and compliant commission payments for sales and customer success representatives. The Manager will oversee the maintenance of an Incentive Compensation Management (ICM) tool, 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.

Responsibilities

• 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.
• 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.

Requirements

• 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.

Skills

• 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.

Schedule

This role is fully remote for candidates who reside outside the 30-mile radius of one of our offices. For candidates within a 30-mile radius, this role is hybrid and requires 3 days a week (Tuesday, Wednesday, Thursday) in the office.

Pay

The US base salary range for this role is $80,900—$224,900 USD. Actual compensation packages are based on factors unique to each candidate, including skill set, depth of experience, certifications, and specific work location. The total compensation package may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Benefits

• Health, dental, and vision coverage beginning on the first day of employment (Five9 covers 100% of the employee portion and shares a high portion of the dependent cost).
• Short- and Long-Term Disability, Basic Life Insurance, and a 401k savings plan with employer matching.
• Access to an innovative mental health support platform offering personalized care and resources (e.g., therapy, coaching, self-guided mindfulness exercises) for all covered employees and dependents.
• Generous Employee Stock Purchase Plan.
• Paid Time Off, company-paid holidays, paid volunteer hours, and 12 weeks of paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.