Senior Manager, Payroll

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?

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.

What You'll Own

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, 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

What We're Looking For

• 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; CPP (Certified Payroll Professional) certification strongly preferred

Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 markets (NYC/ SF), the on-target earning (OTE) pay range for this role is $146,500 - $183,000 USD.

For all other U.S. locations, Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the Tier 1 states listed above, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location.

Life at Flex

We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.

Offices

Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.

Benefits

For full-time U.S. employees we offer:

• Competitive medical, dental, and vision
• Company equity
• 401(k) plan with company match 
• Unlimited paid time off + 13 company paid holidays
• Parental leave 
• Flex Cares Program: Non-profit company match + pet adoption coverage
• Free Flex subscription

 For full-time non-U.S. employees, we offer:

• Competitive compensation + company equity
• Unlimited PTO