Senior Payroll Manager

About us

Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide.

About The Role:

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.

What you'll do:

• 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
• Who you are: 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