Senior Manager, Payroll

Flex•New York, NY

13h•$146,500 - $183,000•Hybrid

About The Position

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.

Requirements

7+ years of progressive, hands-on payroll management experience with direct ownership of multi-state processing, tax compliance, and controls — ideally including at least one role where you built or significantly transformed a payroll function
Demonstrated AI-forward mindset: you actively use AI tools to improve your work, and you have a vision for how AI and automation can transform the payroll function — not just streamline it at the margins
Deep command of U.S. payroll tax law, multi-state compliance, and year-end processes; international payroll familiarity is a plus
Proven experience with equity compensation payroll — stock option exercises, RSU vesting, and related tax withholding and reporting
Strong understanding of payroll internal controls, segregation of duties, and audit requirements; experience designing SOPs and control frameworks in a company scaling toward SOX compliance
Hands-on experience with Rippling or comparable modern HRIS/payroll platforms; comfort evaluating and implementing new payroll technology and AI-powered tools
Startup DNA — you've operated in a high-growth, high-ambiguity environment and know how to build infrastructure while keeping the trains running
Solutions-oriented and proactive; you escalate early, communicate clearly, and don't wait for perfect conditions to make progress
Strong cross-functional instincts and the ability to work effectively with People Operations, Accounting, Legal, and Treasury as true partners
Ability to translate complex payroll and compliance topics clearly for non-specialist audiences including Finance leadership and the CFO
Bachelor's degree in Accounting, Finance, or a related field

Nice To Haves

CPP (Certified Payroll Professional) certification strongly preferred

Responsibilities

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
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
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
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
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
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
Manage and develop the Payroll Coordinator, providing direction, coaching, and performance feedback
Build the payroll team thoughtfully as Flex scales — making the case for additional capability when needed and fostering a culture of continuous learning, including active adoption of AI tools