Senior Manager of Payroll, Flex
$146.5-183k
OTE
+ Equity
More information about location
2-3 days a week in office
Flexible rent payment application
Open for applications
Flexible rent payment application
501-1000 employees
Open for applications
$146.5-183k
OTE
+ Equity
More information about location
2-3 days a week in office
501-1000 employees
Company mission
To help people pay for the things that matter most.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
Many people struggle to pay their rent every month, with a variety of bills hitting their bank accounts simultaneously. Whilst many of these people earn enough money to cover their bills, the inflexible nature of monthly bills can make the all-in-one payment a harder obstacle.
Flex provides a mobile application for the flexible payment of rent, allowing users to pay their landlords through flexible payment plans, reschedule payments when necessary, and protect their funds through Overdraft Protection. The company achieves this by partnering with estate agents and paying their resident's bills upfront, taking on the challenges that landlords would normally have due to late payments.
Flex has experienced extremely rapid growth since its founding which has caused some issues, as it struggled to keep up with the surge in new customers. Having made improvements to its product and scaled its customer service team, it is set to continue providing a service that has come to be highly valued by both tenants and landlords.
Freddie
Company Specialist at Welcome to the Jungle
Insights
10% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2022
$160m
SERIES C
Apr 2021
$46.6m
SERIES B
Total funding: $225.1m
Company benefits
- Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
- Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
- NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
- 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
- Flex Giving: Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
- Employee Assistance Fund: Confidential financial support to teammates facing unexpected hardships or emergencies.
- Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter.
- Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
- Free Flex Subscription: As a Flex employee, you'll have full access to our services without charge.
- GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead.
Company HQ
Midtown Manhattan, New York, NY
Leadership
Shragie Lichtenstein
(Co-Founder & CEO)Prior to co-founding Flex in 2019, Shragie co-founded Boundless Reality. They graduated from Yeshiva University in 2015 with a Bachelor's Degree in Finance.
YeTong Shao
(Co-Founder)Prior to co-founding Flex in 2019, YeTong co-founded Boundless Reality alongside Shragie. They graduated from the University of Chicago with a Bachelor's Degree in Mathematic & Economics.
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