Payroll Operations Manager, Americas - Oyster

About Oyster

Oyster is a global employment platform that lets companies hire, pay, and care for brilliant people anywhere. We are a fully remote, distributed team across 60+ countries, proving that a high-performing culture doesn't need an office.

Role Summary

The Payroll Operations Manager (Americas) is a technically credible people leader who will shape and scale payroll operations across the region. You will lead an experienced distributed team, own operational escalations and vendor outcomes, and partner across the business to improve controls, customer experience, and service delivery. The role requires deep US and Canada payroll expertise, working knowledge of key Latin American markets, strong equity-payroll knowledge, and an automation-first approach to growth.

Key Responsibilities

• Team Leadership: Lead, coach, and develop experienced payroll ICs through clear goals, candid feedback, thoughtful delegation, and effective performance management.
• Technical Escalation: Act as the technical escalation point for complex US and Canada payroll matters and provide informed coverage across Mexico, Brazil, Colombia, and emerging Americas markets.
• Operations & Risk: Own operational escalations, customer calls, root-cause analysis, risk identification, and durable corrective actions.
• Vendor Management: Manage vendor outcomes, SLAs, controls, scorecards, and accountability; challenge recommendations when needed.
• Process Scaling: Build scalable processes, documentation, coverage plans, metrics, and operating rhythms.
• Cross-Functional Partnership: Partner across Product, Finance, Accounting, Legal, and Lifecycle Operations to solve end-to-end problems.
• Efficiency & Automation: Drive automation, standardization, simplification, delegation, and elimination of low-value manual work.
• Expansion Support: Support Americas expansion while sustaining payroll accuracy, timeliness, compliance, and customer trust.

Core Requirements

• Deep US and Canada payroll expertise, including multi-state and provincial compliance.
• Practical exposure to Mexico, Brazil, and Colombia payroll operations.
• Strong equity-payroll knowledge.
• Expertise in payroll controls, reconciliation, risk, escalation management, root-cause analysis, and SLA/KPI ownership.
• Proven vendor-management and vendor-accountability experience.
• Experience leading senior, experienced payroll ICs without micromanaging.
• Evidence of process improvement with concrete, measurable outcomes.
• Remote or distributed people-leadership experience.
• Ability to move fluently between technical detail and regional strategy in an ambiguous, scaling environment.

Bonus / Nice-to-Have Experience

• Deep Latin America payroll experience.
• Puerto Rico, Guam, or other US-territory payroll knowledge.
• EOR (Employer of Record) or global employment experience.
• In-house payroll implementation or vendor-to-in-house migration experience.
• Payroll transformation and Product or Technology partnership experience.
• Advanced practical use of AI and automation in payroll operations.

How We Work & Benefits

• Work from anywhere: Oyster has no borders or HQ. Work from home, forever.
• Paid time off: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.
• Mental health support: Access Plumm, our mental well-being service.
• Wellbeing allowance: Receive a monthly wellbeing allowance in your ThanksBen wallet.
• Flexible parental leave: All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months.
• WFH stipend: Receive a stipend for your laptop and home office equipment.