Senior Manager, Payroll

About the role

Flex is seeking an experienced and operationally strong Senior Manager of Payroll to build and lead our payroll function. This is a newly defined role created to establish payroll as a best-in-class, audit-ready function within Finance - and it's an opportunity for someone who thrives on building from the ground up in a high-growth environment. You will own end-to-end payroll processing and compliance for our 500+ person workforce across multiple jurisdictions, reporting directly to the VP Controller. This is a hands-on leadership role: you'll be both the strategic architect of our payroll operating model and the person responsible for making sure it runs flawlessly every cycle. You'll bring a technology-forward mindset, identifying opportunities to leverage AI and automation to eliminate manual work, reduce error risk, and build a payroll function that scales efficiently through Flex's next stage of growth. You'll work closely with People Operations and the broader Finance and Accounting team to ensure payroll is tightly controlled, accurately reflected in the financial statements, and positioned for scale. This is a hybrid role with an expectation of 2-3 days per week in our New York City headquarters.

Responsibilities

• Payroll Processing & Execution
• Own end-to-end payroll processing for a U.S.-based workforce of 500+ employees, including salary, variable compensation, off-cycle payments, bonuses, commissions, and severance
• Ensure every payroll cycle is accurate, timely, and compliant - with zero tolerance for errors on the fundamentals
• Validate payroll registers against inputs provided by People Operations, maintaining clear segregation of duties between input ownership and processing execution
• Own payroll funding and cash release in coordination with Treasury
• Continuously evaluate opportunities to automate and streamline payroll workflows using AI tools and platform capabilities within Rippling and connected systems
• Tax & Regulatory Compliance
• Own all federal, state, and local payroll tax filings and remittances - including Forms 941, state equivalents, W-2s, and 1099s
• Manage multi-state payroll compliance across all jurisdictions where Flex has employees, staying current on regulatory changes
• Lead resolution of any payroll-related tax notices, audits, or agency inquiries
• Oversee year-end compliance processes including W-2 issuance and EEO filings
• Controls, Process Design & Audit Readiness
• Design and implement a robust, audit-ready payroll control framework - including formal approval workflows, segregation of duties, and escalation protocols
• Develop and maintain comprehensive process documentation and SOPs; leverage AI tools to keep documentation current and accessible
• Reconcile payroll clearing accounts monthly and support the Accounting team's close process
• Build toward SOX-ready standards ahead of a formal requirement
• Technology & Automation
• Serve as the internal owner of Rippling's payroll configuration and capabilities, identifying and implementing features that reduce manual touchpoints
• Partner with Finance and People leadership to evaluate and deploy AI-powered tools for payroll reconciliation, anomaly detection, and compliance monitoring
• Bring a continuous improvement mindset - regularly assess where human effort can be replaced or augmented by intelligent automation without compromising control integrity
• Equity Award Payroll
• Ensure proper payroll tax withholding and timely processing for equity award transactions, including stock option exercises and RSU vesting events
• Partner with Accounting on the financial reporting and journal entry treatment of equity-related payroll activity
• Cross-Functional Collaboration
• Partner closely with People Operations on payroll inputs - compensation changes, new hires, terminations, and leave-related pay adjustments - maintaining clear handoff protocols and input deadlines
• Collaborate with the People Operations benefits team to ensure benefits deductions are processed accurately in payroll
• Work with Legal and Finance leadership on payroll implications of equity programs, workforce changes, or new geographies
• Support external auditors during annual audit cycles
• Team Leadership
• Manage and develop the Payroll Coordinator, providi

Benefits

Additional Information

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It's hard to believe that it's 2026 and paying rent on time is expensive, inflexible, and difficult. We're here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?

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