Senior Payroll Manager

We are hiring our first internal Payroll Senior Manager as Pomelo Care transitions from a PEO to bringing all payroll services in-house and implementing a new HRIS (Rippling). This is a hands-on, high-visibility role for someone who can independently own accurate, compliant, multi-entity payroll for our organization of over 500 employees, while partnering closely with our outsourced payroll/implementation vendor during the transition and, longer term, building and leading an internal payroll team. This role is ideal for a detail-oriented payroll professional who enjoys both the operational rigor of running payroll and the strategic work of standing up a new function from the ground up.

This role reports to the Controller and can be based anywhere in the continental US.

Own end-to-end payroll operations across two legal entities, processing four payroll cycles per month with a high degree of accuracy and independence across both salaried and hourly employees

Serve as the primary Finance internal owner of the PEO-to-Rippling transition, partnering with our People team and outsourced payroll vendor throughout implementation and the first year of operation to ensure a smooth, compliant cutover including data migration, and employee communication / training

Ensure timely and accurate payroll tax filings and payments (federal, state, and local) across all applicable jurisdictions and entities

Oversee timely and accurate processing of benefits-related payments and deductions, including 401(k)/retirement contributions, health and welfare premiums, and other employee benefit withholdings

Maintain payroll system configuration in Rippling, including pay groups, earnings/deduction codes, tax jurisdictions, and general ledger mapping

Serve as the payroll administrator for Rippling, owning system configuration, security/role-based permissions, workflow and approval routing, integrations, and troubleshooting for payroll-related modules

Establish and maintain a strong internal control environment over payroll, including segregation-of-duties, approval workflows, access controls, and documented procedures

Partner with Accounting to ensure payroll data is reconciled, accurately coded, and reflected in financial reporting, journal entries, and month-end/quarter-end/year-end close

Act as the go-to resource for employee pay-related inquiries, resolving issues with professionalism, discretion, and a strong customer-service mindset

Collaborate cross-functionally with the People, Legal, and Accounting teams to support audits, respond to data requests, and continuously improve payroll processes and controls

Stay current on federal, state, and local payroll tax and wage-and-hour regulations, proactively flagging compliance risks and driving remediation

Build the foundation for a scalable, internally-run payroll function, including documentation of processes and controls

Prepare for and ultimately hire, onboard, and manage a Payroll Coordinator/Specialist to support anticipated growth

Bachelor’s degree in Accounting, Finance, Business (or equivalent experience); a CPP certification is highly preferred

7 - 8+ years of progressive, hands-on, multi-state and multi-entity payroll experience at a similarly sized organization

Admin-level expertise with modern HRIS platforms (Rippling is a significant plus), combined with direct experience leading system implementations and / or transitioning away from a PEO

Direct experience with payroll tax compliance, filings, and remittances, and comfort serving as the organization's internal payroll compliance expert

Experience implementing and maintaining strong internal controls and supporting audits

Subject matter expertise in benefits administration as it relates to payroll (401(k), health/welfare deductions, leave payments, garnishments)

Previous people-management experience or a clear readiness to hire, mentor, and lead a direct report as we bring payroll fully in-house.

Strong Excel skills and a high comfort level working with complex payroll and general ledger data

Patient, clear communication skills with the ability to explain payroll matters to employees with empathy and discretion, while building strong partnerships with internal stakeholders and external vendors

Exceptional attention to detail, the ability to operate independently, navigate ambiguity, make sound judgment calls, and build processes from scratch

By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup that always puts the patient first. You will learn, grow and be challenged, and have fun with your team while doing it.

We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first.

By joining Pomelo, you’ll get in on the ground floor of a fast-moving, well-funded startup on a mission to improve outcomes for all mothers and babies. We cultivate a collaborative, patient-first environment where data drives our decisions and team members are challenged to learn, grow, and have fun together.

We believe that solving critical healthcare problems requires perspectives as diverse as the communities we serve. Pomelo is committed to hiring and supporting a team of varied backgrounds, welcoming all applicants regardless of race, age, sexual orientation, gender identity and expression, national origin, religion, disability, or veteran status.